Gambling losses are the main other itemized deduction: losses are deductible on Schedule A, line 16, but only to the extent of winnings for the year. The reporting discipline is strict in both directions. Winnings go on the income line in full, losses go on Schedule A separately, and netting the two before reporting is forbidden. A taxpayer with $5,000 of winnings and $9,000 of losses reports $5,000 of income and deducts $5,000; the extra $4,000 of losses is lost, with no carryforward.
The annuity case carries its own final-return rule: if a retiree dies before the entire annuity investment is recovered tax free, the unrecovered investment is deductible on the retiree's final return.
Many similar expenses are not deductible. Miscellaneous itemized deductions are the deductions that would have been subject to the 2%-of-adjusted-gross-income limitation, and, apart from the qualified-employee exception for unreimbursed employee expenses, deductions in that class can no longer be claimed. Tax preparation fees on the return for the year in which they are paid are one member of that class and can no longer be deducted, including software, publications, and electronic-filing fees. The diary rule backs the gambling numbers. The taxpayer keeps a contemporaneous diary recording four details for each wager: (1) the date and type of the wager, (2) the name and location of the establishment, (3) the names of the companions present, and (4) the amounts won or lost. Estimates reconstructed at year-end do not satisfy the requirement, so a client who gambles regularly should start the diary before the losses accumulate.
Worked example
Karl itemizes, reports $5,000 of winnings, and documents $9,000 of losses in a diary meeting all four detail tests. He deducts $5,000 on Schedule A and gets no benefit from the other $4,000. He also pays $300 for tax preparation software for the year. That fee is a miscellaneous itemized deduction of the 2% class and is no longer deductible, so it adds nothing to Schedule A. Had his diary been missing the companions' names, the $5,000 deduction could be disallowed, since the taxpayer must keep an accurate diary and the diary must contain at least the listed information.