I think if you have Jessica join/spy on the club that voids the MC's ability to join the Witchcraft club on their own. I could be wrong!
Additionally, I suspect if the MC rejects Raven's quarterback skill transfer spell, then that removes the MC from the Witchcraft club path too (also could be wrong).
As for your other bugs, if you can bullet point them and tag
Vim!, it's quite plausible they'll be fixed in a future release (if not already fixed in the not-yet-publicly available SubscribeStar release).