I proceeded as above in the third example and was able to get my MA return accepted. It's bad form on the part of TT that anyone who a) has traded options and b) needs to file a massachusetts return cannot file without overriding the appropriate data. The fix is mathematically correct but not really how the trades work, which is why the brokerages report them as they do. This got it done for me this year, but requiring customers to edit or override correctly reported data is really bad form, and anyone who meets the above criteria will probably not use TT in the future.
