For anyone who has landed here, I'll update my original message above with some more tips:
- First, the UI is completely broken as I mentioned. However, it is more broken for E*Trade than it is for Schwab. I have accounts in which I traded options at each bank, and only E*Trade's imported data led to the disaster described above.
- The Schwab option trade data which did _not_ throw errors was auto-imported as sales of "stock (non-employee)." Let me repeat that: the data was _incorrectly_ imported as stock, not as options. But this incorrect import seemed to lead to _correct_ data entry in terms of gains and dates. I did not have to go in and manually verify each one. This also means that I might advise others to select "stock" rather than "options" when manually correcting your E*Trade options sales. Similarly, if you want to keep using TurboTax, you should probably stop using E*Trade. Unfortunately, I don't know which banks (other than Schwab) to recommend instead.
- Finally, on a lighter note, I started treating the manual updating of my 116 E*Trade transactions as a game. Load transactions, scroll to 5 page selector button, select page number, scroll up to required review item, click into item, update dropdown sale type, update dropdown how obtained, update how disposed, update cost basis, confirm no special situations apply, confirm zero basis, hit Continue. This process took me about 90 seconds per transaction at first, but then I got it down to 45 seconds each, then 30 seconds each. So I wound up spending more than 58 minutes but less than 174 minutes on this one step. If a product manager is reading this, I recommend adding this stat to your KPIs.
