> Jellyfin forced me to organize my files into Show/Season folders, whereas Plex just handled my original flat mess of scattered files.

You keep all your shows in a single directory? or just sorted into folders per show?

I haven't had any issues with files just sorted into show folders for shorter series, but even in general it's very un-particular about filenames as long as you have `<show name> (<year>) S<Season #>E<Episode #>` (and it accepts a decent number of formats for season/episode number, and year is usually only needed if you need to differentiate shows with the same name).