Generally, prepaid medical expenses, including dental costs, are not deductible. An old Tax Court case said that advance payment for medical services to be rendered in the following year are not deductible in the year paid. The only exception is for prepaid of lifetime care from a continuing care facility or nursing home.
Fully deductible interest on up to two residences if acquisition debt secured by a home is $1 million or less, and home equity debt is $100,000 or less.