Even after all the back and forth, the core issue was never resolved. The import of the 1099-B or any tax documents from Schwab never happened, although the pop up's suggested they were. In talking to a human yesterday (TurboTax expert Hal), he suggested entering the key data from the 1099 into my TurboTax return, as the IRS really doesn't need all the specifics of the actual stock transactions. Up side is after doing that, I believe my Schwab aspect of the return is complete. Down side is I now have to send in the specifics via snail mail with IRS form 8453: an act not required if the download were successful. I've used TurboTax (downloaded, not via online) for 20+ years and never before had an issue that Intuit could not resolve, which is disappointing.
