The amount of premiums for a long-term care policy that are treated as a deductible medical expense if you itemize deductions is based on your age as of the end of the year. The fact that you paid a lump sum for the policy does not change the amount deductible for the year in which you make the payment. Note: Check on special rules that may apply for state income tax purposes, which may be different from federal income tax treatment.
A capital loss that is not deductible because it exceeds the annual $3,000 capital loss ceiling. A carryover loss may be deducted from capital gains of later years plus up to $3,000 of ordinary income.