

It’s a small piece in your observation but I’ve been on the hunt for an android client for jellyfin with downloads that are… usable. Fladder has been so far the only one where this seemed to work okay-ish (it’s still slow, and I noticed it doesn’t detect if the device supports Dolby vision to force transcoding). But still, if your one user is still trying… maybe it helps them a lil.
I think there is no comprehensive guide because people have varying opinions on what’s “best”. IMO the “best” for everyone is the way that they understand how things work and are comfortable to manage it, regardless of how good or bad someone else says that is.
My recommendation is to just accept you will not get it right first time, you’ll eventually face the issues and limitations of whatever way you picked and have to either rebuild or adapt.
Personally, I’d say choose a starting path of do you want to learn about the various technologies and have maximum potential (and, problems to solve) or do you just want to get some of the common apps running and don’t care how as long as they run and be limited by what’s available, but with much fewer issues. Path 1 is following the docker/proxmox path and it may take a lot of reading and watching YouTube tutorials before you get somewhere, path 2 is aiming for something like casaOS or similar and probably watching their getting started will get you results faster but if something breaks or is not available, you may get stuck.
Last, pick 1 thing that’s your goal and work on getting that there. There is no right order, but the more popular something is the more resources there will there be. https://selfh.st/apps/ is a great resource for finding things. Jellyfin is actually pretty easy to start with and gives you some good paths forward around it (e.g. start with you manually getting your media in the right place, then you can work on adding other apps that will do it for you). I’d advise to avoid self hosting email, it’s rather difficult.
Once you grasp how things work, it becomes a shopping mall of just add what you want, it’s just climbing that hill at least once that’s hard if you’re not from a tech background.