> Jellyfin forced me to organize my files into Show/Season folders

Regarding this, try out sonarr/radarr with hard links.

No don't, sonarr is definitely worse if you have a unstructured media folder. I currently use it and its good, but I remember when first starting out with pile of files in semi random folders it being a mess to start up. Like some of the restrictions of the bulk importer made very little sense. Also, sonarr is tied to a single metadata provider which sometimes makes very unpopular decisions about the naming of series and episodes. When pluribus was initally released, they insisted on naming the series "plur1bus" even though no other source, imdb or even AppleTV used that as the official name. This broke auto downloading for the season.

Does sonarr/radarr fix not having to use Show/Season structure?