The log file is from the Plex client, not the server. See Reporting issues with Plex Media Server for information on obtaining Plex server logs.
Not sure why things are reverting to unmatched after you manually match things. However, your naming structure is definitely contributing to things.
Plex is very picky with TV shows. Rename your files according to Plex requirements.
After renaming, it may be necessary to Plex Dance the entire show.
If you’ve many shows to rename (you mention nine), take a look at FileBot. It has templates for Plex and can make quick work of renaming hundreds of movies/shows.
An example, copied from another post, but still applicable:
\TV Shows <-- TV Library points here. Name does not matter.
..\Ace Attorney
....\Season 01 <-- "Season" must be in English
......\Ace Attorney - s01e01.ext <-- ext = mkv/mp4/etc
If you want to keep the “quality.lots.of.extraneous.info,” put it at the end of the file name. Plex ignores everything after sxxeyy. Ex: show_name - sxxeyy - episode_name [quality.lots.of.extraneous.info].ext
If you use the new Plex TV show scanner, you can add the show’s TVDB ID to the folder name to assist in matching.
\TV Shows <-- TV Library points here. Name does not matter.
..\Ace Attorney {tvdb-305077}
....\Season 01 <-- "Season" must be in English
......\Ace Attorney - s01e01.ext <-- ext = mkv/mp4/etc
