Is there a way to find out exactly what is causing a specific file to not play?

Just as I thought.
These subtitles are in PGS format. (ripped from Bluray)
Very few players can understand this format. So when you play such a file in Plex, the server will try to burn-in the subtitles into the video picture, because it knows that your client won’t be able to display the subs otherwise = Transcoding

To avoid that,

N.B. you may want to take a look at Naming and Organizing Your TV Show Files | Plex Support because with file names like the above you will run into “matching” issues with Plex, sooner or later.