That is a bit of a gamble. As you said, we don't know what will happen with the standard deduction. Even without that though, the medical deduction is not a dollar for dollar deduction. Unless further changes are made to the tax code the medical deduction is subject to an income limitation. Medical expenses must first be reduced by 7.5% of your adjusted gross income. The percentage was 10% at one time. This means that if you have $50,000 in adjusted gross income the first $3,750 (50,000 x 7.5%) of your medical expenses are not deductible. If you spend $12,000 in insurance premiums your deduction would only be $8,250.
To compound this we go back to the overall standard deduction vs itemized deduction issue. Since you are living in a paid off condo you will have no mortgage interest. Under the 2021 standard deduction amount ($25,100) you would need $13,250 (25100-8250) in property taxes, state taxes, charitable contributions, and other allowable itemized deductions before you could deduct any of your medical expenses.
