Gregory G. Boree v. Commissioner of IRS , 837 F.3d 1093 ( 2016 )


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  •                Case: 14-15149       Date Filed: 09/12/2016      Page: 1 of 29
    [PUBLISH]
    IN THE UNITED STATES COURT OF APPEALS
    FOR THE ELEVENTH CIRCUIT
    ________________________
    No. 14-15149
    ________________________
    Agency Docket No. 029549-11
    GREGORY G. BOREE,
    MELANIE M. BOREE,
    Petitioners–Appellants,
    versus
    COMMISSIONER OF THE INTERNAL REVENUE SERVICE,
    Respondent–Appellee.
    ________________________
    Petition for Review of a Decision of the
    United States Tax Court
    ________________________
    (September 12, 2016)
    Before MARTIN and JORDAN, Circuit Judges, and COOGLER, * District Judge.
    COOGLER, District Judge:
    *
    The Honorable L. Scott Coogler, United States District Judge for the Northern District
    of Alabama, sitting by designation.
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    This is an appeal from a decision of the United States Tax Court (the “Tax
    Court”) sustaining a determination by the Commissioner of the Internal Revenue
    Service (“Commissioner”) of deficiencies in the 2007 income tax return of
    Appellants Gregory and Melanie Boree (“the Borees”). The Tax Court ruled that
    the Borees were liable for a deficiency of $1,784,242 due to an improper
    characterization of income from the sale of property as a capital gain rather than as
    ordinary business income and imposed a 20% penalty for substantial
    understatement of income tax pursuant to § 6662 of the Internal Revenue Code (the
    “I.R.C.”). After careful review of the record and briefs of the parties, and having
    the benefit of oral argument, we affirm the Tax Court on the issue of the Borees’
    tax liability but reverse the Tax Court’s imposition of the statutory penalty.
    I.    BACKGROUND
    In November 2002, Gregory Boree (“Mr. Boree”), a former logger, and a
    partner, Daniel Dukes (“Dukes”), doing business as Glen Forest, LLC (“Glen
    Forest”), acquired 1,892 acres of vacant real property formerly owned by
    International Paper in Baker County, Florida. Glen Forest bought the property for
    $965 per acre, for a total of $3.2 million, and borrowed much of the funds needed
    to purchase it. In December 2002, Glen Forest sold one ten-acre parcel of the
    property to an individual purchaser.
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    In January 2003, Glen Forest submitted to the Baker County Planning and
    Zoning Department a conceptual map of a planned residential development called
    West Glen Estates, which would consist of more than 100 lots, to be developed and
    sold in multiple consecutive phases. The following month, the county adopted the
    proposal and rezoned the West Glen Estates property into ten-acre lots. Glen Forest
    also petitioned the Baker County Board of Commissioners to exempt West Glen
    Estates from county platting requirements so that it could continue to sell lots
    without completing interior roads or submitting plans to the board. During 2003,
    Glen Forest sold approximately fifteen lots located around the perimeter of the
    West Glen Estates property.
    On February 18, 2003, Mr. Boree also executed a Declaration of Covenants,
    Conditions, and Restrictions for West Glen Estates which, among other things,
    created a homeowners association to maintain roads within the subdivision. The
    declaration consistently referred to Glen Forest as the “developer” of West Glen
    Estates and provided Glen Forest the right to elect at least one member of the
    homeowners association’s board of directors as long as the “[d]eveloper holds for
    sale in the ordinary course of business at least five percent (5%) of the acreage in
    all phases of the property.” The declaration applied to the entire 1,892 acres of the
    Glen Forest property and did not distinguish between lots with frontage on county
    roads or other lots.
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    During the remainder of 2003 and through 2004, Glen Forest engaged in a
    series of other development activities, including obtaining county approval of the
    first three phases of development of West Glen Estates, applying for an
    Environmental Resource Permit, establishing and recording easements in
    collaboration with the local water and electrical utilities, and constructing Braxton
    Road, an unpaved road on the property, at a cost of roughly $280,000. However,
    Glen Forest did not install water lines, sewer lines, electrical lines, gas lines,
    telephone lines, cable lines, or a storm drainage system. Nor did it pave any roads,
    perform any grading or landscaping work, or build any structures on the property.
    Glen Forest did not have a sales office for West Glen Estates or hire a broker to
    sell lots, but it did place classified advertisements for the subdivision in local
    papers from time to time. During 2004, Glen Forest sold approximately twenty-six
    lots.
    Beginning in late 2004, the Baker County Board of Commissioners adopted
    a series of land use restrictions that affected West Glen Estates. In October 2004,
    the board adopted a temporary one-year moratorium on the development of non-
    platted subdivisions. In November 2004, it adopted another temporary one-year
    moratorium on development along certain county roads, including Cowpen Road,
    which ran adjacent to the West Glen Estates property. In December 2004, the
    board adopted a third temporary one-year moratorium on the development of any
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    platted subdivisions containing dirt roads. In April 2005, it adopted a requirement
    that all roads within subdivisions be paved. West Glen Estates was a non-platted
    subdivision that contained multiple unpaved roads. Mr. Boree testified that
    complying with the requirement that Glen Forest pave internal roads in West Glen
    Estates would have cost roughly $7 million.
    The Borees assert that in 2005, Glen Forest sold approximately eight lots. 1
    In March 2005, Dukes sold his interest in Glen Forest to Mr. Boree. Then, Melanie
    Boree (“Mrs. Boree”) succeeded Dukes as the second member of the LLC. Mr.
    Boree then requested an exception for the “whole parcel” of his property to the
    April 2005 ordinance requiring that roads in subdivisions be paved, but he was
    unsuccessful.
    After his request was denied, Mr. Boree hired a land-use lawyer to pursue a
    different strategy. His new strategy included a higher-density development plan for
    West Glen Estates that would justify having to bear the costs of paving the roads
    imposed by the county’s requirements. Mr. Boree testified that his intention was to
    1
    The Tax Court found that the Borees sold seventeen lots in 2005. The Borees dispute
    the Tax Court’s findings as to how many lots they sold for the years 2005 and 2006. The
    discrepancy apparently stems from the Borees’ practice of entering into a type of seller financing
    called an “Agreement to Deed,” where the Borees would hold the deed as security for the
    purchase price and not record it until the purchaser fully paid the debt, which might occur years
    after the property was first sold. Thus, the Tax Court’s finding that seventeen lots were sold in
    2005 appears to be based on the execution of deeds related to lots that were actually sold in years
    prior. Because the exact number of lot sales the Borees closed in 2005 and 2006 is not
    dispositive with regard to our analysis, we will assume that the Borees entered into only eight
    new sales agreements for lots in 2005.
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    “up-zone” the property to make it more appealing to other developers who might
    be interested in purchasing the property from him. With his attorney’s help, Mr.
    Boree prepared and submitted applications in May and June 2005 to rezone the
    West Glen Estates property to accommodate the denser “Planned Unit
    Development.” This new Planned Unit Development proposal related to 982 acres
    of the original West Glen Estates property and included a densely zoned residential
    area, a 10.8-acre commercial zone, a 44-acre recreational parcel with equestrian
    amenities, and paved internal roads. However, the preliminary maps did not
    include any roads leading to the development. In April 2006, the Borees’ attorney
    appeared on behalf of Mr. Boree before the Baker County Board of
    Commissioners, where he advised the Northeast Florida Regional Planning
    Council that Mr. Boree was planning a “large-lot subdivision with associated
    commercial to serve the neighborhoods” with a 40-acre “equestrian facility and
    bridle trails throughout the residential subdivision.” The attorney, on behalf of Mr.
    Boree, requested that the county adopt a new land use designation of “rural
    commercial,” never before used in Baker County, for the proposed 10.8 acres of
    commercial property. The board ultimately adopted the new land use category.
    In January 2006, the county adopted a requirement that developers pave
    certain public roads leading to their subdivisions. Mr. Boree testified that
    complying with the requirement that Glen Forest pave connecting county roads
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    would have cost an additional $4.4 million. The Borees assert that they did not sell
    any lots in 2006.2
    Around that time, the Borees discovered that a successful Miami developer,
    Adrian Development (“Adrian”), was planning a large-scale development on a
    parcel of property adjoining the West Glen Estates property. In April 2006, Mr.
    Boree negotiated a real estate purchase agreement with Adrian, whereby Adrian
    would purchase nearly all of Mr. Boree’s remaining unsold West Glen Estates
    property, totaling over 1,067 acres, for a price of no less than $9,000 per acre.
    In June 2006, Mr. Boree’s attorney again appeared before the county board
    on Mr. Boree’s behalf at a public hearing on the rezoning action for the West Glen
    Estates Planned Unit Development. The attorney confirmed to the board that the
    West Glen Estates lots, earlier sold by Mr. Boree, all had access to ingress–egress
    roads. He also represented that Mr. Boree had originally wanted to sell the interior
    lots with access to a gravel road, but that, in response to the ordinance requiring the
    paving of subdivision internal roads, he had pursued the higher-density plan.
    Lastly, the attorney explained that Glen Forest had changed ownership, and he
    referred to Glen Forest as “the development entity that originally owned all this
    land and sold off some of it.”
    2
    The Tax Court found that Glen Forest sold four lots in 2006. Again, however, three of
    these appear to be deed executions in completion of earlier-executed sales agreements. The
    fourth “sale” in 2006 was actually a sales agreement entered into by the Borees that was never
    effectuated. See note 1, supra.
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    In August 2006, the county recommended approval of the West Glen Estates
    Planned Unit Development, on the condition that Glen Forest pave the private
    Braxton Road and certain other county roads that transected the property.
    However, in late September 2006, Glen Forest withdrew the Planned Unit
    Development proposal and indicated its intent to rezone the West Glen Estates
    property into 7.5-acre agricultural lots for a “residential subdivision.”
    On February 6, 2007, Adrian closed the purchase of the remaining West
    Glen Estates property consisting of 1,067.63 acres for $9,608,670, or roughly
    $9,500 per acre. The sales agreement referred to the property as “unimproved.”
    The property sold to Adrian included tracts from approved phases I through III of
    the West Glen Estates subdivision, tracts that were part of the proposed Planned
    Unit Development, and lots in the remaining acreage. One week after the sale,
    Glen Forest withdrew its pending rezoning application from the county.
    In all, between 2002 and 2006, Glen Forest sold approximately sixty lots
    comprising approximately 600 acres of its original 1,892 acres. During that time
    period, Glen Forest’s only business activities involved sales and development
    related to the property. Glen Forest never made any distributions to its members.
    Rather, it used all proceeds to pay the carrying costs of the property.
    The Borees employed the firm Austin Bovay, P.A. for tax matters and return
    preparation. Mr. Boree had been using Mr. Bovay, the founding CPA of the Bovay
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    firm, since 1998. Mr. Bovay was also a tax professor at the University of Florida
    Levin College of Law Master’s in Taxation program. Ms. Messal, an employee in
    the Bovay office, handled the Borees’ tax returns, and the Borees testified that she
    was extremely detail-oriented. Mrs. Boree testified that she entered all of the sales
    information and other data related to the maintenance of the property into
    QuickBooks and then provided that to Ms. Messal. In the years 2002, 2003, and
    2004, Glen Forest reported on its K-1 Schedules that it had sustained ordinary
    (non-capital) losses on the sale of lots from the West Glen Estates property, and
    that Mr. Boree’s share of such losses exceeded $100,000. In the years 2005, 2006,
    and 2007, Glen Forest reported the activities associated with Glen Forest on each
    Schedule C “Profit or Loss from Business” form. The Borees did not capitalize the
    costs associated with the West Glen Estates property, but instead characterized
    those costs as ordinary and necessary business expenses and took deductions for
    them. More specifically, the Borees deducted expenses of $293,445 in 2005;
    $138,168 in 2006; and $46,360 in 2007 for Glen Forest. The Borees also claimed
    on their Schedule C “Profit or Loss from Business” form ordinary losses of
    $147,196 in 2005; ordinary losses of $63,228 in 2006; and ordinary losses of
    $15,633 in 2007, as their business expenses exceeded their business income in
    each of those years. Although the Borees took deductions of $46,360 for ordinary
    and necessary business expenses in 2007, they nevertheless reported the gain
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    ($8,578,636) from the sale to Adrian as a long-term capital gain, rather than as
    ordinary income, on their 2007 tax return.
    On September 27, 2011, the Commissioner issued the Borees a deficiency
    notice pursuant to § 6212 of the I.R.C. relating to their 2007 income tax return.
    Specifically, the Commissioner found that the Borees’ income from selling the
    West Glen Estates property to Adrian should have been characterized as ordinary
    income, rather than as a capital gain, resulting in a $1,784,242 tax deficiency.
    Additionally, the Commissioner imposed a penalty under § 6662(b)(2) of the
    I.R.C. in the amount of $356,848.40 for substantial understatement of income tax.
    On December 27, 2011, the Borees filed a petition with the Tax Court asking
    it to redetermine their tax liability and remove the statutory penalty. During a two-
    day bench trial in 2013, the Borees testified that Mr. Boree purchased the West
    Glen Estates property intending primarily to hold it as an investment and that he
    sold perimeter lots only to make payments on the debt he incurred to purchase the
    property. While the Tax Court expressed an inclination to find the Borees’
    testimony credible at the conclusion of the trial, it later issued a nine-page opinion
    noting that the documentary evidence “convincingly contradicted” Mr. Boree’s
    testimony and revealed that his true intent was to develop the property for sale in
    the ordinary course of business. The Tax Court explained that the Borees
    “consistently treated Glen Forest as a business” by such activities as subdividing
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    the West Glen Estates property, building a road, spending significant time and
    money on zoning activities, and continuing to pursue development activities after
    the board had adopted the moratoria on unpaved roads. The court added that the
    Borees consistently represented Glen Forest as a real estate business to the buyers
    of its property, to the county board, and on their 2005, 2006, and 2007 tax returns.
    It also noted that between 2002 and 2006, the Borees made frequent and
    substantial sales of property to customers in the ordinary course of business. Even
    after the Borees took full control of Glen Forest, the court noted, they “continued
    to engage in significant sales and development activities; reported their sales of
    lots [in 2005] as ordinary income; deducted, rather than capitalized, expenses
    relating to their real estate activities; and did not segregate the property sold to
    Adrian from the rest of the [West Glen Estates] property.” The court thus found
    that the Borees’ “actions from the time Glen Forest acquired the [West Glen
    Estates] property, through the date of the Adrian transaction, reflect their intent to
    develop [that] property and sell subdivided lots to customers.” The Tax Court thus
    concluded that the Borees were not entitled to capital gains treatment on their 2007
    tax return. The court further ruled that they were liable for the 20% statutory
    penalty because they had “not established reasonable cause for the underpayment
    or that the return was prepared in good faith.”
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    The Borees timely appealed. This Court has jurisdiction to review the
    decision of the Tax Court under I.R.C. § 7482.
    II.        STANDARDS OF REVIEW
    This Court “review[s] the Tax Court’s legal conclusions de novo, and its
    factual findings for clear error.” Gustashaw v. Comm’r, 
    696 F.3d 1124
    , 1134 (11th
    Cir. 2012). The determination of whether income derived from the sale of property
    is subject to taxation as ordinary income or as a capital gain is a “legal
    conclusion.” Suburban Realty Co. v. United States, 
    615 F.2d 171
    , 180 (5th Cir.
    1980). 3 However, it is a question of fact whether the taxpayer intended to hold the
    property primarily for sale in the ordinary course of business or for investment
    purposes. 
    Id.
     at 180–81. “Whether a taxpayer acted with reasonable cause and in
    good faith with regard to an underpayment of tax is a question of fact that we
    review for clear error.” Gustashaw, 696 F.3d at 1134.
    III.   DISCUSSION
    A.     Whether the Tax Court Correctly Held that the Borees’ Gain
    from the 2007 Sale of 1,067 Acres of Real Property was Taxable
    as Ordinary Income and Not as a Capital Gain
    The I.R.C. distinguishes between ordinary income and capital gains.
    “Income representing proceeds from the sale or exchange of a capital asset that a
    3
    Decisions of the former Fifth Circuit issued prior to October 1, 1981, are binding
    precedent on this Court. See Bonner v. City of Prichard, 
    661 F.2d 1206
    , 1207 (11th Cir. 1981)
    (en banc).
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    taxpayer holds for over a year is considered a capital gain and is taxed at a
    favorable rate.” Long v. Comm’r, 
    772 F.3d 670
    , 675 (11th Cir. 2014) (per curiam).
    The purpose behind capital gain treatment is to “ameliorate the hardship of
    taxation of the entire gain in one year.” Comm’r v. Gillette Motor Transp., Inc.,
    
    364 U.S. 130
    , 134, 
    80 S. Ct. 1497
    , 1500 (1960). However, “[o]ther income, or
    ‘ordinary income,’ is taxed at a higher rate.” Long, 772 F.3d at 675. “[T]he term
    ‘capital asset’ means property held by the taxpayer (whether or not connected with
    his trade or business), but does not include . . . property held by the taxpayer
    primarily for sale to customers in the ordinary course of his trade or business.” Id.
    (quoting I.R.C. § 1221(a)(1)). Because capital gains treatment “is an exception
    from the normal tax requirements of the Internal Revenue Code, the definition of a
    capital asset must be narrowly applied and its exclusions interpreted broadly.”
    Corn Prods. Ref. Co. v. Comm’r, 
    350 U.S. 46
    , 52, 
    76 S. Ct. 20
    , 24 (1955).
    To determine whether property is a “capital asset” within the meaning of §
    1221 of the I.R.C., the Fifth Circuit enumerated a list of factors:
    (1) the nature and purpose of the acquisition of the property and the
    duration of the ownership; (2) the extent and nature of the taxpayer’s
    efforts to sell the property; (3) the number, extent, continuity and
    substantiality of the sales; (4) the extent of subdividing, developing,
    and advertising to increase sales; (5) the use of a business office for
    the sale of the property; (6) the character and degree of supervision or
    control exercised by the taxpayer over any representative selling the
    property; and (7) the time and effort the taxpayer habitually devoted
    to the sales.
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    United States v. Winthrop, 
    417 F.2d 905
    , 909–10 (5th Cir. 1969); see Sanders v.
    United States, 
    740 F.2d 886
    , 889 (11th Cir. 1984) (applying the Winthrop factors).
    No factor or combination of factors is controlling. Biedenharn Realty Co. v. United
    States, 
    526 F.2d 409
    , 415 (5th Cir. 1976) (en banc). Rather, each case must be
    decided on its particular facts. 
    Id.
     Still, the “frequency and substantiality” of sales
    is the “most important” of these factors. Id. at 416. This is because “the presence of
    frequent sales ordinarily belies the contention that property is being held ‘for
    investment’ rather than ‘for sale.’” Suburban Realty Co., 
    615 F.2d at 178
    .
    Despite the Tax Court discussing several of the Winthrop factors in reaching
    the determination that the Borees’ 2007 income was ordinary income, and not a
    capital gain, the Borees nonetheless raise several points on which they assert the
    court legally and factually erred.
    1.     The Tax Court’s consideration of the Borees’ purpose in
    holding the property from the time it was acquired until the
    sale to Adrian in 2007
    The Borees first argue that their purpose in holding the West Glen Estates
    property changed from development to investment as a result of the Baker County
    land use restrictions in 2005 and 2006, which made further development so
    expensive as to be practically impossible, and that it was thus error for the Tax
    Court to have considered their purpose in holding the property at any time other
    than at the moment of their bulk sale to Adrian. However, in Suburban Realty Co.,
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    the Fifth Circuit rejected the notion that “the decisive question is the purpose for
    which (the property) ‘primarily’ was held when sold.” 
    615 F.2d at 182
     (emphasis
    added). Rather, the court reasoned, “At the very moment of sale, the property is
    certainly being held ‘for sale.’ The appropriate question certainly must be the
    taxpayer’s primary holding purpose at some point before he decided to make the
    sale in dispute.” 
    Id.
     The court thus analyzed the taxpaying entity’s purpose in
    holding the property over multiple years prior to its sale, finding that although the
    company originally acquired the property as an investment, it engaged in such
    frequent sales through a ten-year period that its primary purpose changed to “for
    sale” at some point during that time. 
    Id.
     at 183–85. While the Borees would have
    us focus instead on this Court’s statement in the subsequent case of Sanders v.
    United States that “it was the taxpayer’s intent at the time of the sales that is
    relevant for an inquiry as to whether capital gains treatment is justified,” 
    740 F.2d at 889
    , Sanders is not at all inconsistent with Suburban Realty Co. The Sanders
    court also analyzed the taxpayer’s activities over multiple years in sustaining the
    Tax Court’s decision that the taxpayer’s income was ordinary income, finding that
    although the taxpayer’s original purpose was not to establish a real estate business,
    by the time he earned the profits at issue in the years 1974 and 1975, he had been
    engaging in the business of subdividing land, making improvements, and selling
    lots for several years. 
    Id.
     Thus the “sales” the Sanders court referred to in the
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    above-quoted statement were the taxpayer’s “continuous and frequent sales of the
    lots over the period from 1972 to 1976.” 
    Id.
     Far from diverging from Suburban
    Realty Co.’s direction to look at the circumstances leading up to the sale, the
    Sanders court actually did the same thing, in fact citing Suburban Realty Co. as its
    source. See id.4 Thus, we find no legal error in the Tax Court’s consideration of the
    Borees’ intent during the years leading up to the sale. We think that a proper
    analysis of a taxpayer’s primary purpose in holding property should take into
    account a reasonable period of time prior to the sale, if for nothing else but to
    determine whether the taxpayer’s intent changed.
    In determining whether property is held for sale in the ordinary course of
    business within the meaning of § 1221(a)(1) of the I.R.C., considerations include
    (1) whether the taxpayer was engaged in a trade or business, and if so, what
    business; (2) whether the taxpayer was holding the property primarily for sale in
    that business; and (3) whether the sales contemplated by the taxpayer were
    ‘ordinary’ in the course of that business. Suburban Realty Co., 
    615 F.2d at 178
    .
    There is no real dispute at this point that prior to the enactment of the county land
    use restrictions, Glen Forest held the West Glen Estates property for sale in the
    4
    Nor could the Sanders panel reach a holding directly inconsistent with that of Suburban
    Realty Co. without violating our Circuit’s laws. See, e.g., Cargill v. Turpin, 
    120 F.3d 1366
    , 1386
    (11th Cir. 1997) (“The law of this circuit is ‘emphatic’ that only the Supreme Court or this court
    sitting en banc can judicially overrule a prior panel decision.”), cert. denied, 
    523 U.S. 1080
    , 
    118 S. Ct. 1529
     (1998).
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    ordinary course of the business of developing a subdivision. 5 When Glen Forest
    acquired the West Glen Estates property in 2002, it began subdividing and selling
    lots immediately. Soon thereafter, Glen Forest began seeking approval for
    subdivision of the property and submitted plans for development in multiple
    phases. Within a few months, the Borees executed covenants and restrictions for
    the entire property, which identified Glen Forest as the “developer” of West Glen
    Estates, and provided Glen Forest a board position in the homeowners association
    as long as the “[d]eveloper holds for the sale in the ordinary course of business at
    least five percent (5%) of the acreage in all phases of the property.” Mr. Boree
    repeatedly represented West Glen Estates to the Baker County Board of
    Commissioners and the Northeast Florida Regional Planning Commission as a
    planned residential subdivision. Through all of its efforts, including building an
    expensive unpaved road, obtaining various permits, creating easements, setting up
    a homeowners association, and submitting development plans in multiple phases to
    the board for approval, Glen Forest always identified itself as the “developer” of
    the project.
    According to the Borees, however, they abandoned all intent to develop the
    property after the paving requirements were imposed, and they liken their case to
    5
    Although Mr. Boree testified at trial that he always intended to hold the property for
    investment and that his holding purpose never changed, he now argues that his purpose changed
    as a result of altered circumstances.
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    others in which an “adverse government action” renders the taxpayer’s original
    purpose futile. For instance, they rely on Ridgewood Land Co. v. Commissioner, in
    which the taxpayer acquired property intending to develop and sell it in the
    ordinary course of business. 
    477 F.2d 135
    , 136 (5th Cir. 1973) (per curiam). The
    State of Mississippi then authorized condemnation proceedings against the
    property for use in the construction of a highway. 
    Id.
     Under threat of
    condemnation, the taxpayer sold the property to an adjacent landowner who was
    negotiating to sell the land to the state for inclusion in the highway project. 
    Id.
     In a
    decision the court emphasized was based on the “the particular facts of the case,”
    the court found that the taxpayer’s purpose in holding the property had changed
    from ordinary course of business to investment because any development of the
    land would have been futile due to the impending condemnation. 
    Id.
     That case is
    distinguishable, however, because an exercise of the government’s eminent domain
    power, unlike an ordinance mandating the paving of roads, deprives a landowner
    of all potential uses of his property except selling the property to the government.
    It was appropriate for the court to conclude in Ridgewood Land Co. that because
    the property was condemned, the taxpayer lost the opportunity to develop it, and
    therefore had no other purpose for holding the property aside from investment. The
    Baker County paving requirements, however, merely placed additional costs on
    developers interested in pursuing certain types of development. The restrictions did
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    not foreclose all development of property in Baker County. Potential developers
    just had to be financially able to pave internal and connecting roads. As such,
    “adverse government action” cases like Ridgewood Land Co. are of no help to the
    Borees.
    More importantly, even if we were to focus only on the Borees’ intentions
    for the property after the land use restrictions were imposed in 2004 and 2005,
    their actions in the years 2004 through the sale in 2007 betray their true intent to
    continue to develop the property. When compliance with the moratoria threatened
    to render the original West Glen Estates development plan unprofitable, Mr. Boree
    did not passively hold the property in hopes that he could sell it to a buyer at an
    attractive price, but instead first sought to obtain exceptions to the paving
    requirements so that his subdivision could proceed. When that was unsuccessful,
    he hired a land-use attorney and applied to rezone the property for a more densely
    zoned residential and commercial development that would fund his costs of
    complying with the new county paving requirements. Indeed, Mr. Boree was
    successful in persuading the county board to create a new land use designation of
    “rural commercial,” never before used in the county, for part of the Planned Unit
    Development. The Borees assert that the fact that their preliminary maps of the
    Planned Unit Development had no roads leading to it reveals that it was a mere
    hypothetical and that they were only trying to “up-zone” the property to make it
    19
    Case: 14-15149      Date Filed: 09/12/2016    Page: 20 of 29
    more attractive to a buyer in hopes of selling it in bulk, but they offer no
    explanation for the fact that they continued to pursue the Planned Unit
    Development strategy even after they entered into the sales agreement with Adrian
    in April 2006. Indeed, at the June 2006 meeting of the Baker County Board of
    Commissioners, Mr. Boree’s attorney confirmed that the Planned Unit
    Development had been undertaken to justify the paving costs imposed by the
    county restrictions and that Glen Forest, “the development entity that originally
    owned all this land and sold off some of it,” was the same developer who owned
    the remaining acreage. Such evidence of strategic and thorough involvement in
    pursuit of developing the property indicates that the Borees were holding the
    property for sale in the ordinary course of business right up until they sold it to
    Adrian, and not merely as an investment property. Not only that, but the Borees
    continued to sell, or attempt to sell, some lots to individuals after the land use
    restrictions were first imposed in 2004, and they deducted (instead of capitalized)
    expenses related to the property in 2006 and 2007. Thus, the Tax Court’s factual
    finding that the Borees “continued to pursue development activities after the board
    adopted the moratoriums and requirements” was not clearly erroneous.
    2.     The Tax Court’s determination that the Borees did not
    segregate the property ultimately sold to Adrian
    The Borees’ second argument is that the Tax Court essentially ignored Mr.
    Boree’s testimony that he always segregated the interior acreage ultimately sold to
    20
    Case: 14-15149     Date Filed: 09/12/2016    Page: 21 of 29
    Adrian from the perimeter lots that Glen Forest regularly sold to individuals,
    treating the former as an investment asset and the latter as inventory merely to
    generate funds to pay off his debt.
    A taxpayer may hold some property for sale in the ordinary course of
    business and some for investment, but
    the burden is on the taxpayer to establish that the parcels held
    primarily for investment were segregated from other properties held
    primarily for sale. The mere lack of development activity with respect
    to parts of a large property does not sufficiently separate those parts
    from the whole to meet the taxpayer’s burden.
    Suburban Realty Co., 
    615 F.2d at 185
    . Whether a taxpayer segregated property for
    investment as opposed to inventory purposes would appear to be a question of fact,
    just as is the taxpayer’s overall primary purpose for holding the property. See 
    id.
     at
    180–81 (“[T]he question of taxpayer’s purpose or purposes for holding the
    property is primarily factual, as is the question of which purpose predominates.”).
    There was no error in the Tax Court’s factual determination that the Borees
    “did not segregate the property sold to Adrian from the rest of the [West Glen
    Estates] property.” The Borees argue that they never platted the large interior
    parcel and that the sales agreement with Adrian described it as “unimproved,” but
    all of the maps and development plans for West Glen Estates that the Borees
    originally provided to the Baker County Board of Commissioners included all of
    the acreage, and nowhere set aside or separated out the acreage later sold to Adrian
    21
    Case: 14-15149      Date Filed: 09/12/2016    Page: 22 of 29
    from the ten-acre lots that were sold to individuals over the years. Indeed, of the
    acreage ultimately sold in bulk in 2007, eighty to ninety acres had been included in
    phases I to III of the initial West Glen Estates development plan. Early maps of the
    project envisioned the entire property divided into ten-acre lots, and Mr. Boree
    sought an exemption from the county paving requirements for the “whole parcel.”
    Later, the plans for the Planned Unit Development encompassed the entire acreage,
    undermining Mr. Boree’s argument that he changed his primary purpose in holding
    the property after the county required paving.
    3.     The Tax Court’s alleged failure to consider that the Borees’
    gain resulted solely from market appreciation
    The Borees next argue that the Tax Court erred in failing to find dispositive
    the fact that their $8 million profit in 2007 was due to the property appreciating in
    value over a substantial period of time and was not reflective of any improvements
    made to the property or other efforts on the part of Glen Forest in conducting
    ordinary business activities. However, the Fifth Circuit rejected the notion that just
    because an increase in property value is attributable more to market appreciation
    than to improvements made to the property, that the taxpayer is automatically
    entitled to capital gains treatment. Suburban Realty Co., 
    615 F.2d at 186
     (rejecting
    the notion that “all gains emanating from appreciation in value over a substantial
    period of time are to be treated as capital gains”). Rather, the court stated that the
    converse is true: “i.e., that capital gain treatment will be proper only if the gain
    22
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    emanates from appreciation in value. Instances of gain emanating from
    appreciation being treated as ordinary income are not inconsistent with this
    proposition.” 
    Id.
     The Borees’ fortuitous sale of their property to Adrian in 2007
    was not entitled to capital gains tax treatment simply because the property had
    appreciated in value, when the sale arose from their engaging in the ordinary
    course of the business of developing real estate.
    4.     The Tax Court’s treatment of the Winthrop factors
    The Borees’ final argument is that the Tax Court “misapplied” two of the
    Winthrop factors and failed to consider others. First, they say that if the “number,
    extent, continuity and substantiality of sales,” Winthrop, 
    417 F.2d at 910
    , is
    considered the most important factor, see Biedenharn Realty Co., 526 F.2d at 416,
    then the Tax Court should have also considered that they sold far fewer lots after
    the county imposed the paving restrictions, which they say proves that they
    abandoned any intent to develop the property in favor of the bulk sale to Adrian.
    The Tax Court understandably found that the sale of approximately sixty lots
    comprising approximately 600 acres and over one-third of the property the Borees
    acquired in 2002 constituted “frequent and substantial” sales. Even if three of the
    four sales the Tax Court attributed to 2006 were merely the executions of deeds
    that the Borees held as security for the purchase price of lots sold in earlier years,
    the fact remains that individual purchasers continued to acquire lots from Glen
    23
    Case: 14-15149      Date Filed: 09/12/2016    Page: 24 of 29
    Forest in 2006, contrary to the Borees’ contention that all business operations
    ceased. Further, Glen Forest engaged in no income-producing activity other than
    the sales of lots over the years. See Suburban Realty Co., 
    615 F.2d at
    179 n.24
    (“The taxpayer’s claim to capital gain treatment is likely to be weaker if he can
    point to no other business activities; i.e., if close to 100 percent of his income is
    derived from sales of real estate.”). Additionally, even if the Borees did not close a
    single sale in 2006, they still sought to develop their property by creating and
    presenting the Planned Unit Development to the county board, which would
    increase the value of lots in future sales, and they continued to report sales of lots
    each year as ordinary business income on their tax returns.
    Second, the Borees argue that the Tax Court misapplied the second
    Winthrop factor, “the extent of subdividing, developing, and advertising,” 
    417 F.2d at 910
    , by failing to consider that Glen Forest did not advertise West Glen Estates
    beyond the small classified ads abandoned before the ordinances were imposed and
    that it never installed water, sewer, or electricity, and built only one dirt road on
    the property. However, the evidence discussed by the Tax Court is of development
    activities over a period of time. Perhaps the development activities were not as
    extensive as in other cases, or perhaps different inferences could be drawn from the
    facts. However, we discern no error related to the Tax Court’s application of the
    second Winthrop factor.
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    Finally, the Borees argue that the Tax Court erred as a matter of law by not
    considering the remaining Winthrop factors, which they say tilt in their favor.
    However, they have not cited any authority requiring courts to address each and
    every factor. In fact, Winthrop itself states, “Despite their frequent use . . . these
    seven [factors] ‘in and of themselves . . . have no independent significance, but
    only form part of a situation which in the individual case must be considered in its
    entirety . . . .’” 
    417 F.2d at 910
     (quoting Cole v. Usry, 
    294 F.2d 426
    , 427 (5th Cir.
    1961)). We do not think that the factors are meant to be mechanically applied so as
    to disallow a court from viewing the evidence in its totality and drawing
    appropriate inferences from that evidence. For example, the Tax Court, we think
    appropriately, appeared to give great weight to the fact that the Borees deducted
    expenses related to the property from 2002 to 2007, a practice inconsistent with
    capital gains treatment, even though the deduction of expenses is not contemplated
    in the Winthrop factors.
    As we do not find any of the Borees’ arguments in support of reversal
    meritorious, the Tax Court’s determination of their tax liability will be affirmed.
    B.     Whether the Tax Court Correctly Sustained the Imposition of a
    Statutory Penalty for Substantial Understatement of Income Tax
    The Borees’ second request on appeal is for the reversal of the Tax Court’s
    imposition of the substantial understatement penalty. While § 6662 of the I.R.C.
    imposes a 20% accuracy-related penalty on taxpayers for “[a]ny substantial
    25
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    understatement of income tax,” I.R.C. § 6662(b)(2), the penalty shall not be
    imposed with respect to any portion of the underpayment “if it is shown that there
    was a reasonable cause for such portion and that the taxpayer acted in good faith
    with respect to such portion.” I.R.C. § 6664(c)(1). It is the taxpayer’s burden to
    establish that he acted with reasonable cause and good faith. Calloway v. Comm’r,
    
    691 F.3d 1315
    , 1334 (11th Cir. 2012).
    A court’s determination of a taxpayer’s reasonable cause must be “made on
    a case-by-case basis, taking into account all pertinent facts and circumstances.”
    
    Treas. Reg. § 1.6664
    –4(b)(1). The most important factor in this determination is
    the “extent of the taxpayer’s effort to assess [his] proper tax liability.” 
    Id.
    “Reliance on . . . professional advice . . . constitutes reasonable cause and good
    faith if, under all the circumstances, such reliance was reasonable and the taxpayer
    acted in good faith.” Id.; see also Gustashaw, 696 F.3d at 1139 (“A taxpayer may
    meet his burden by showing that he reasonably relied in good faith on the advice of
    an independent professional, such as a tax advisor, lawyer, or accountant, as to the
    transaction’s tax treatment.”). “The taxpayer’s education and business experience
    are relevant to the determination of whether the taxpayer’s reliance on professional
    advice was reasonable and done in good faith.” Gustashaw, 696 F.3d at 1139
    (citing 
    Treas. Reg. § 1.6664
    –4(c)(1)). The Supreme Court recognized in United
    States v. Boyle, 
    469 U.S. 241
    , 251, 
    105 S. Ct. 687
    , 692–93 (1985), that a taxpayer
    26
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    exercises “ordinary business care and prudence” when he reasonably relies on his
    accountant’s advice on matters beyond a layperson’s understanding:
    When an accountant or attorney advises a taxpayer on a matter of tax
    law, such as whether a liability exists, it is reasonable for the taxpayer
    to rely on that advice. Most taxpayers are not competent to discern
    error in the substantive advice of an accountant or attorney. To require
    the taxpayer to challenge the attorney, to seek a “second opinion,” or
    to try to monitor counsel on the provisions of the Code himself would
    nullify the very purpose of seeking the advice of a presumed expert in
    the first place.6
    To be eligible for the reasonable cause and good faith exception, the
    taxpayer must also show that his professional’s advice was based on “all
    pertinent facts and circumstances and the law as it relates to those facts and
    circumstances.” 
    Treas. Reg. § 1.6664
    –4(c)(1)(i). Further, the advice relied
    upon must not be based on any “unreasonable factual or legal assumptions,”
    and must not “unreasonably rely on the representations, statements, findings,
    or agreements of the taxpayer or any other person.” 
    Id.
     § 1.6664–4(c)(1)(ii).
    The Tax Court did not elaborate on why it found that the Borees did not
    establish reasonable cause or that their tax return was prepared in good faith,7 and
    the record does not support the court’s conclusion. Mr. Boree, a former logger with
    6
    The Supreme Court’s discussion is dicta because it is unnecessary to the holding in that
    case, which is that a taxpayer’s failure to make a timely filing of his tax return is not excused by
    his reliance on an agent, and such reliance is not “reasonable cause” for a late filing under §
    6651(a)(1) of the I.R.C. Id. at 252, 
    105 S. Ct. at 693
    .
    7
    The Tax Court’s wording implies that one may establish reasonable cause or good faith
    to comply with § 6664(c)(1), but the statute actually requires both. I.R.C. § 6664(c)(1).
    27
    Case: 14-15149       Date Filed: 09/12/2016      Page: 28 of 29
    no accounting experience, had relied on the Bovay accounting firm since 1998, a
    firm that enjoyed a strong reputation due in part to Mr. Bovay serving as a tax
    professor at the University of Florida Levin College of Law. But see 
    Treas. Reg. § 1.6664
    –4(c)(1) (“[R]eliance may not be reasonable or in good faith if the taxpayer
    knew, or reasonably should have known, that the advisor lacked knowledge in the
    relevant aspects of Federal tax law.”). Mrs. Boree testified that the Borees never
    had any cause to question the advice of their accountant until this case. Mrs. Boree
    personally provided Ms. Messal in the Bovay firm, whom she described as
    extremely detail-oriented, with the information and records she kept relating to all
    of the land transactions, indicating that the Borees engaged in appropriate efforts to
    assess their tax liability. There is no indication in the record that the Borees
    withheld any information from their accountant, and the Commissioner conceded
    at oral argument that the Borees did not provide any false information. Although
    the Borees’ accountant prepared the 2007 tax return claiming deductions of
    $46,360 for business expenses while claiming a capital gain from the same
    activity, we find that it was reasonable for the Borees, who were untrained in tax
    matters, to have relied in good faith on that decision. The Tax Court clearly erred
    in finding that the Borees did not establish reasonable cause and that the return was
    prepared in good faith. 8
    8
    Because we so hold, we need not address the Borees’ alternative defense against the
    28
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    IV.    CONCLUSION
    The Tax Court correctly concluded that the Borees were liable for the tax
    deficiency. We thus affirm the Tax Court on the issue of the Borees’ tax liability
    for the year 2007. However, we find clear error in the Tax Court’s determination
    that the Borees failed to establish that they acted with reasonable cause and in good
    faith. Accordingly, the Tax Court’s assessment of the substantial understatement of
    income tax penalty is reversed.
    AFFIRMED IN PART AND REVERSED IN PART.
    imposition of the penalty, which is that they had substantial authority for their tax treatment
    pursuant to § 6662(d)(2)(B)(i) of the I.R.C.
    29