I suspect the problem is the file naming and/or folder structure. You have the season folders including a year in brackets, so Plex is looking for a TV series named “The Season.” The year works best when it’s included in the series title… Also include the series name before the season/episode identification. Something like this will probably work better:
Show Name (YYYY)\Season 01\Show Name - S01E01 - Episode Title
Chances are you will have to Plex Dance the files to make it work properly.
