Sorry to say that I did not figure out how to do this systematically or through the upload of my 1099-B brokerage data. Back when I posted this I was in the process of filing an amended return because I didn't realize the data didn't transfer to my PA return correctly before filing (I was in a rush and never had that problem before in almost 10 years of using TT!). When I filed my amended return I just dumped all my brokerage data into Excel and made it look like PA Schedule D so I could manipulate each line to reflect the correct G/L and cost basis, etc.
Unfortunately I'm dealing with the same issue for my 2020 tax return, which is why I haven't filed yet. I too have hundreds of lines of trades, and quite frankly it is very annoying that TT can't import major brokerage data correctly for my state return.
