The 2,000 limit error message in TT Deluxe Desktop happened when only attempting to do an import of about 50 transactions from another Fidelity brokerage account.
I went the route of starting a return in TT Premier Online so I could import 2,067 1099-B sales from one of my Fidelity accounts (turns out I didn't have 3,500 after all -- that was just an estimate based on the # of pages in the PDF). Then I exported the Online .tax file to my computer and opened it up in TT Deluxe Desktop. There was the Fidelity 1099-B's 2,067 line items in all their glory. OK, I thought, I'll now continue with the imports from my other brokerage accounts. It wouldn't allow me to import any of them as it could see my working Desktop return already contained more than 2,000 transactions. So that must be a hard cap that they have imposed, along with the new error message prompting me to bail out and request a refund.
So I suppose my only option is to continue with TT's Online Premier product. It seems to be the only route for those of us having more than 2,000 1099-B transactions.
I did some research on H&R Block's options for those of us with a high # of transactions. It seems they limit you to 250-500 line items if you use their Desktop product. However, their Online tax software allows an "unlimited" number:
https://www.mybrokerageinfo.com/app/literature/view?itemCode=9894698&renditionType=pdf
Everything is moving to the cloud, and "desktop" software is quickly becoming a dinosaur. We see clearly that both TT and H&R are giving emphasis and expanded capabilities to their online products, so us Desktop users should probably get with the times.
