1. Your 1099-R should normally have some sort of indicator if it is a pick-up contribution. See this Maryland webpage.
Note that in other years, taxpayers have noted that the 1099-R issued by the state doesn't match the TurboTax input screen, but I think you can tell which is which is you look for Pickup on the 1099-R.
If there anything in box 19?
2. "This same screen is also asking me for the, "Maryland Distribution Amount."" - was there nothing in box 16 on the 1099-R? Yes, the Maryland distribution is normally the same as the gross distribution, but that number should have been on box 16.
You might call the agency that sent you the 1099-R and ask them why there is nothing on box 16.
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