Maybe run through the installation again, and run via Docker if you aren’t already. It was plug-and-play when I set it up

Alternatively, obsidian offers a 1st party paid sync feature

Obsidian livesync works really well. Notes are live synced between my desktop and Android device

https://github.com/vrtmrz/obsidian-livesync

I’ve been considering switching to Jellyfin for a while due to concerns about Plex either becoming worse or them peering into my library. Any idea how the apps work on Fire TV Stick? I have one for home and one I take away with me and it all works seamlessly with Plex