1 - No, you can only add attachments to a paper return filed by mail.
2 - After you have entered your Form 1099-R reporting the early distribution from your IRA or retirement plan, there will be a series of follow-up questions. Then, there will be more follow-up questions after you leaving the Form 1099-R summary page. One of those questions will be a screen showing many different options available to reduce or eliminate the early distribution penalty. There will be a box there for medical expenses paid (in excess of 7.5% of AGI). This is where you enter the amount paid for medical costs that exceeded 7.5% of your AGI on the return.
@rogowske
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