So to follow up:
As I’m sure you all expected, it turned out to be as simple as the naming after all. That {plex} tag in FileBot (which admittedly I barely understand but got to work nonetheless, let me rename all of my Naruto seasons (blessedly the hard part has been done already and I didn’t have to Bulk Rename or manually match anything cause the names were close enough) really quickly. I did the Plex Dance (this still cracks me up, but as an avid retro gaming enthusiast I totally get it), and when I updated my library after that, everything is perfect. I didn’t have to delete any of the cache files. Now because I’m a perfectionist I have to go about renaming my entire library and reimporting, even though this problem hasn’t occurred anywhere else using #x# naming convention. Thanks again for all the explanations and advice, and maybe more importantly, making my first post on this forum a good one. 
I subbed I to Plex I think over a year ago and I still feel like I’m living in the future when I’m streaming cartoons from my own pc to my phone or console etc. So I got no beef at all with having to name stuff a certain a way.
