I installed Jellyfin on my home server a few months ago but it’s already broken by upgrading to 10.11, and unusable until I restore 10.10 from backup or start over: https://github.com/jellyfin/jellyfin/issues/15027. There seem to be lots of other database migration bugs for this release and other ones.
I use Docker on Linux for this kind of thing (Jellyfin, Nextcloud and a few others) and updates are completely trouble free. I would never deploy complex "black box" apps like Jellyfin bare metal. That being said, I do run my email stack bare metal as I want fine control. Everything is hosted at home on my own hardware and I would never consider moving my computing to the "cloud."
Update: I just tried upgrading again (from 10.11.1 to 10.11.2) and it seems to have fixed things!
Yeah, I've been afraid to upgrade because I've been following these updates. I'm going to wait until the dust settles a bit before upgrading because, as stated, I don't really enjoy larping as a sysadmin anymore.