For good medical reasons, your doctor strongly (and in writing) advises you that you need to start doing daily swimming pool laps ASAP, working up to 25 laps per day over the next 12 months if possible. All fine and good . . . except that the closest public pool is more than 40 miles from your house, which is way out in the country You pay $25,000 for a backyard lap pool, which is finished and paid for on April 1^st. Then you start paying $100 per month for pool boy maintenance. Are any of these costs deductible as Schedule A medical expenses why or why not? And if (but only if) you say yes, how would you calculate the deductible amount?