Id run your library thru a rename process. I always include the imdb id in the filename, that way the matching issues are prevented. Update the naming, then plex dance them.
My canned response is to see https://support.plex.tv/articles/naming-and-organizing-your-tv-show-files/ and:
If you want to save yourself a lot of time I would recommend using Download - tinyMediaManager and use ${title} (${year}) {imdb-${imdb}} as the new name format.
Folder format:
${title} (${year})
(Please note I linked to the v3 which is free to use)
