[jurialmunkey]

I thought I could just remove/delete the show from my library and then re add with the above settings checked. However, I now cannot re add the show back to my library at all. I tried but it's a no go. In my userdata log library there's some json log entries that read..."Show last aired more than 3 months ago and no next aired date set next update 2022-12-02" that get logged after trying to re add the show.

First up: TMDbH wont add anything that's already in your library. You must delete the .strm files from your harddrive and then clean the library in "Kodi Settings > Media > Library" before trying to re-add anything.

The next step is to override the "next_check" values that TMDbHelper stores when it adds a tvshow. The "next_check" value is calculated based upon the airing schedule and status of the show to avoid unnecessarily rechecking for new episodes every day. That's the message in the log you're seeing.

Monitored Trakt Lists
If you added shows by monitoring Trakt lists, then the simplest approach is to force the update from settings:
TMDbHelper Settings > Library > Update Library Now > Forced Update

Manually Added Shows from Context Menu
If you added shows individually via the context menu, then you will need to delete the corresponding library autoupdate cache file from the pickle folder before re-adding the show.

You can find these cache files in ".kodi/userdata/addon_data/plugin.video.themoviedb.helper/pickle". Each show is saved in an individual text file in that folder named "library_autoupdate_tv_{tmdbID}". You can get the ID by searching on the TMDb website and looking at the URL e.g. Game of Thrones will be library_autoupdate_tv_1399 because the URL is https://www.themoviedb.org/tv/1399-game-of-thrones