As for 'group totals' I don't recall the specifics but I did this a couple years ago I think you can group all likewise trades, (ie short term/long term/ESPP etc...) just add up everything Paid $10000, sold $11000 etc.. if it was 1 transaction or 100 it doesn't matter. So long as there's no wash sales or anything you're good to go. If you have wash sales you'll need to attach those specifically to the report (it can be the full 1099-B or you can condense only the wash sales to an excel sheet and print it out) you cannot file electronically that way (or you can but you need to snail mail that piece)
I broke the program a couple years ago, I think it only supports 2500 trades in a year (I was like 7k) The 1099-B was almost 500 pages, so mailing that was a non-starter too. I think I used pandas to parse the pdf and spent an hr. or two whittling everything down in excel. Painful but it worked. I think there's help in the software itself about doing some of that.
