Get your taxes done using TurboTax

If the investment income that was reinvested came from a taxable account (i.e., not in an IRA, 401-K, etc.) then yes, it is a taxable dividend.  The TT form for a 1099-DIV (or the import process) has a field for total dividends (box 1a) and for qualified dividends (1b), with boxes that match your 1099-DIV (or consolidated 1099 if it also shows interest and/or transactions, etc.).  So, go back and look at that form where you entered that information - there isn't a separate "question" for it (at least not in the desktop versin.)   [Qualified dividends are a subset of total dividends - sometimes all of the total.] 

199A dividends result from transactions for things like REITs (Real Estate Investment Trusts) and the like - which may be held by a mutual fund.  They also involve form 8995, and *may* be eligible for a 20% deduction which if I recall correctly, TT will handle based on answer to appropriate questions it asks along the line.  For the nitty gritty, see the instructions for IRS form 8995.

 

Medical expense are a specific part of the TT "interview" process.  Note that you cannot deduct medical insurance premiums taken pre-tax out of your salary.  TT asks questions do determine whether or not that is the case.

 

JRJ