I raised this issue with Western Digital but they referred me here.
Mycloud Home Plex as working fine all my movies, TV shows, Photos and music where all indexed - then an update messed it all up.
I re enabled Plex on the Mycloud Home and now my some of my TV shows are not showing at all - some of the ones that are have each season of a show showing as one episode with multiple versions - each “version” being an episode of the show.
My standard response to that is:
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.
Plex has dropped support for several naming schemas over the years. Just because your old non-standard format used to work doesnt mean it will continue to work.
overlapping shows/episodes need split at the show level. However fixing your naming schema is the better solution instead of trying to manually split stuff apart and manually matching them.
My naming schema worked until it didnt too. About 6 months ago plex dropped support for the [SSxEE] naming schema in order to allow people to hide stuff in file names using [ ]. About half my library disappeared before I caught it.