When is it beneficial to list medical expenses?

Contributions to political candidates cannot be deducted. 

Medical expenses can only be deducted if you itemize. 

You cannot deduct donations to political candidates.

Are you itemizing deductions such as mortgage interest and property tax?  Medical expenses are another itemized deduction---but a tough one to use.

MEDICAL EXPENSES

The medical expense deduction has to meet a rather large threshold before it can affect your return. The amount of medical (including dental, vision, etc.)  expenses that will count toward itemization is the amount that is OVER 7.5% of your adjusted gross income. You should only enter the amount that you paid in 2020—do not include any amounts that were covered by insurance or that are still outstanding.  Of course, your medical expenses plus your other itemized deductions still have to exceed your standard deduction before you will see a difference in your tax due or refund.

To enter your medical expenses go to Federal>Deductions and Credits>Medical>Medical Expenses