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"directly connected with or pertaining to the taxpayer's trade or
business" may be deducted. Sec. 1.162-1(a), Income Tax Regs.
Whether an expenditure is ordinary and necessary is
generally a question of fact. Commissioner v. Heininger, 320
U.S. 467, 475 (1943). To be "necessary" within the meaning of
section 162, an expense need only be "appropriate and helpful" to
the taxpayer's business. Welch v. Helvering, 290 U.S. at 113.
For an expense to be "ordinary", "the transaction which gives
rise to it must be of common or frequent occurrence in the type
of business involved." Deputy v. du Pont, 308 U.S. 488, 495
(1940) (citing Welch v. Helvering, supra at 114).
Section 6001 and the regulations promulgated thereunder
require taxpayers to maintain records sufficient to permit
verification of income and expenses. As a general rule, if the
trial record provides sufficient evidence that the taxpayer has
incurred a deductible expense, but the taxpayer is unable to
adequately substantiate the amount of the deduction to which he
or she is otherwise entitled, the Court may estimate the amount
of such expense and allow the deduction to that extent. Cohan v.
Commissioner, 39 F.2d 540, 543-544 (2d Cir. 1930). However, in
order for the Court to estimate the amount of an expense, we must
have some basis upon which an estimate may be made. Vanicek v.
Commissioner, 85 T.C. 731, 743 (1985). Without such a basis, any
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