I've had all my servers running on my personal Windows machine, and I've been planning to move them to a dedicated Linux machine, as well as move to Linux on my PC. Part of that involved containerizing my whole setup to make the move easier. There's a script listed in Jellyfin docs that helps you migrate your setup. Itzs a bit involved if you're coming from Windows but very doable. Very easy if you're already on Linux though.
My media setup is on a Linux VPS configured with Swizzin community edition. I tried a bunch of docker-based projects over the years but could never quite get my head around it. A good friend of mine just redid his whole setup with docker tho, so maybe if/when mine breaks I'll give it another shot.
I definitely struggled to wrap my head around it at first, but I got used to using it when I got into DevOps, and once you understand it, it becomes so easy and helpful that it's easy to overuse it. I can certainly answer any questions to the best of my ability if you do look into it!
I despised the thought of another layer adding to the difficulty of troubleshooting problems, it took me a long time to make myself try it. And sometimes it does make you have to think a bit about what it's doing under the hood but if you commit to it and work with it, it's such a great way to silo your services. I wouldnt' go back now.