What makes Debian a pain to use on servers?

I personally combine lower end NAS boxes with 4x4 mini PC’s. I like the separation of concerns, as well as the tiny footprint.

I use a VPS from RackNerd for all kinds of things (my personal Lemmy, for one). Have had it for two and a half years or so with no complaints.

Ditto. You could also leave Jellyfin as your back end, and link it to Kodi for your front end (if it is just the UI you are bored of)