-46-
testing whether the resulting terms and conditions of a
transaction were the same as if unrelated parties had engaged in
the same transaction.” Estate of Bongard v. Commissioner, supra
at __ (slip op. at 46). Intrafamily or related-party
transactions are not barred under this standard, but they are
subjected to a higher level of scrutiny. Id. at __ (slip op. at
46-47).
In probing the presence or absence of a bona fide sale and
corollary legitimate and significant nontax purpose, courts have
identified various factual circumstances weighing in this
analysis. These factors include whether the entity engaged in
legitimate business operations, whether property was actually
transferred to the entity, whether personal and entity assets
were commingled, whether the taxpayer was financially dependent
on distributions from the entity, and whether the transferor
stood on both sides of the transaction. See, e.g., Estate of
Thompson v. Commissioner, supra; Kimbell v. United States, 371
F.3d 257 (5th Cir. 2004); Estate of Bongard v. Commissioner,
supra; Estate of Hillgren v. Commissioner, T.C. Memo. 2004-46;
Estate of Stone v. Commissioner, T.C. Memo. 2003-309; Estate of
Strangi v. Commissioner, T.C. Memo. 2003-145; Estate of Harper v.
Commissioner, T.C. Memo. 2002-121.
Hence, in evaluating whether decedent’s transfers to Schutt
I and II are properly characterized as bona fide sales, the
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