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Section 213(a) allows a deduction for medical and dental
expenses paid during the year that are not compensated for by
insurance or otherwise but only to the extent that the expenses
exceed a floor of 7.5 percent of AGI.
To substantiate medical and dental expenses, the taxpayer
must furnish the name and address of each payee, the amount, and
the date paid. See sec. 1.213-1(h), Income Tax Regs.; see also
Davis v. Commissioner, T.C. Memo. 2006-272. If requested by the
Commissioner, the taxpayer must furnish an itemized invoice from
the payee that identifies the patient, the type of service
rendered, the specific purpose of the expense, the amount paid,
the date paid, and any other information the Commissioner deems
necessary. See sec. 1.213-1(h), Income Tax Regs.; see also Davis
v. Commissioner, supra; Cotton v. Commissioner, T.C. Memo.
2000-333.
If a taxpayer establishes that deductible expenses were
incurred but has not established the exact amounts, the Court may
estimate the amounts allowable in some circumstances (the Cohan
rule). See Cohan v. Commissioner, 39 F.2d 540, 543-544 (2d Cir.
1930). The Court can estimate the amount of a deductible expense
only when the taxpayer provides evidence sufficient to establish
a rational basis for making the estimate. Vanicek v.
Commissioner, 85 T.C. 731, 743 (1985). Where a taxpayer fails to
provide adequate evidence of his expenses, the Court may uphold
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