[crispyambulance]

  > ...am meticulous at making sure the structure and filenames are correct before dumping anything new to the library to the point where I have a complex script to...

I am the exact opposite, partly because I feel like it SHOULD BE the responsibility of the media library to maintain associations between the media files and their metadata, regardless of the filename.

It seems crazy to me that Plex and other media libraries effectively require you to follow persnickety file-naming conventions. I am very much in the minority of folks who think that you should just be able to point these media servers to a file, tell it what that file is, and then have it maintain associations so you can query your media in arbitrary ways to make a playlist or whatever-- no filenames changes needed.

[ubercow13]

I think you can do that, there is an informal standard for xml files which can live alongside the media with metadata info. I'm not sure if Jellyfin can create them directly but it can read them. See for example tinymediamanager

https://www.tinymediamanager.org/

[crispyambulance]

Tinymediamanager looks really cool. Much nicer than filebot!