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sufficient evidence to establish a rational basis for making the
estimate. See Cohan v. Commissioner, 39 F.2d 540, 543-544 (2d
Cir. 1930); see also Vanicek v. Commissioner, 85 T.C. 731, 742-
743 (1985).
Section 274(d) supersedes the general rule of Cohan v.
Commissioner, supra, and precludes us from estimating the
taxpayer’s expenses with regard to certain items. See Sanford v.
Commissioner, 50 T.C. 823, 827 (1968), affd. per curiam 412 F.2d
201 (2d Cir. 1969). Section 274(d) imposes strict substantiation
requirements for expenses relating to, among other things,
travel, entertainment, and “listed property”, including
automobiles and other property used as a means of transportation.
Sec. 1.274-5T(a), Temporary Income Tax Regs., 50 Fed. Reg. 46014
(Nov. 6, 1985). To obtain a deduction for such items, the
taxpayer must substantiate “by [either] adequate records or
sufficient evidence corroborating * * * [his] own statement” the
amount of the expense, the time and place of travel or
entertainment, the business purpose of the expense, and the
business relationship to the taxpayer of the person entertained.
Sec. 274(d); Beale v. Commissioner, T.C. Memo. 2000-158; sec.
1.274-5(b)(1), Income Tax Regs. To meet the “adequate records
test”, a taxpayer must maintain an account book, diary, statement
of expense, or similar record prepared contemporaneously with the
expenditure and documentary evidence of certain expenditures,
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