I had just under 2000 and the software kept crashing on me, super frustrating. I just ended up doing summary for it.
This was what someone replied to a similar question I had...
If you cannot import the 1099-B you can report summaries instead of individual transactions. Under Let us enter your investment sale info select I'll type it in myself. Later when you Tell us about your 1099-B, choose I'll enter a summary for each sales category. Click the Learn More and How do I? links for assistance. (Click the screenshot below for reference.)
https://ttlc.intuit.com/replies/4926553
