IRS Publication 502 Medical and Dental Expenses page 10 - https://www.irs.gov/pub/irs-pdf/p502.pdf#page=10
Lifetime Care—Advance Payments
You can include in medical expenses a part of a life-care fee or "founder's fee" you pay either monthly or as a lump sum under an agreement with a retirement home. The part of the payment you include is the amount properly allocable to medical care. The agreement must require that you pay a specific fee as a condition for the home's promise to provide lifetime care that includes medical care. You can use a statement from the retirement home to prove the amount properly allocable to medical care. The statement must be based either on the home's prior experience or on information from a comparable home.
Health care insurance premiums and other medical expenses that you paid with out of pocket funds are an eligible medical expense that you can deduct using Schedule A for itemized deductions. However, only your total medical expenses that are greater than 7.5% (2019) of your Adjusted Gross Income (AGI) can be deducted. Your total itemized deductions reported on Form 1040 Schedule A must be greater than the standard deduction for your filing status to have any tax benefit.
Standard deductions for 2019
Single - $12,200 add $1,650 if age 65 or older
Married Filing Separately - $12,200 add $1,300 if age 65 or older
Married Filing Jointly - $24,400 add $1,300 for each spouse age 65 or older
Head of Household - $18,350 add $1,650 if age 65 or older
Enter medical expenses, sch a in the Search box located in the upper right of the program screen. Click on the Magnifying Glass. Click on Jump to medical expenses, sch a
