As someone who meticulously organises media... this was not a problem for either Plex or Jellyfin.
The one thing that gets both of them fucked up for some reason is Ghost Stories, even with the TVDB tag, which should make it a non-issue. Still, it's easy to fix, on both platforms.
My media looks like this:
Movies: [decade][Title as it appears on TVDB] ([Year]) ([Special things like Directors Cut or whatever]) ([Resolution]).mkv
Shows (including anime): [Show Title][Show Title] S[season]E[episode] [Episode title].mkv
Music: [Artist]([Year]) [Album title][Track Number] [Track title].m4a
Oh, another issue you will run into, with shows, is "fan ordering." A good one for this is Sword Art Online. Some very vocal fans hate that there's a fourth season. They don't actually hate the content of the fourth season, they just think it should be combined with the third season for whatever dumb ass reason people on the Internet get incensed about stupid shit. They tried to plead their case on the TVDB forums and got shot down. So if you go by their order, the latter half of the episodes won't be named and won't have descriptions. Then, whenever the fifth season comes out, if you try to call it the fourth season, it'll get the titles and descriptions of the actual fourth season that's out now. So you can't do that.
If you're having issues with TV shows, get an app called Rename My TV Series. It's on Windows, it's on Mac, and it's on Linux. And it's free. Or you could pirate FileBot, I guess. Or pay for it. I'm not your dad. But I'll use free software over warez any day, as long as it does what I need. Why pirate when the free version does just as good? Just like Plex and Jellyfin, RMTVS uses TVDB, so you know your filenames will comply with your media server. And, if you're on Plex (not sure about Jellyfin on this specific one), you can rename the seasons, so you could call Season 4 "Season 3, Part II" and everything will still work. However, I named my SAO seasons "Sword Art Online," "Sword Art Online II", "Sword Art Online: Alicization," and "Sword Art Online: Alicization: War of Underworld." It looks really cool, since that anime doesn't use seasons, each season actually has a slightly different name for the show. (It's probably, if we're being that nit picky, several shows in one franchise, but that's not how TVDB wants it, and Plex won't let you do it that way, either.)





