Maybe self host your own VPN on a VPS and connect the jellyfin server as a client as well as any other devices you want to see that jellyfin server as other clients and configure the VPN server to not override your default routing and to allow clients to see each other? In my head I don’t think that would conflict with your protonVPN connection.

Your traffic would be encrypted between devices so I wouldn’t say https is nessesary and thus no certs needed.

The rubs that occur to me are that I’m not sure you can do this on a free tier VPS which is the only option I see given your financial limitations. And your devices all need to be able to connect to said VPN.

Edit: Slightly less worse English.

Nope. I fiddle until it does what I want. If the thing I’m working on is complex or I’m struggling with it I’ll keep versions of configs. And I back up working configs via an rsync job. Which isn’t a particularly robust solution but I’m content with it for my needs.

That would suck if so since I obviously utilize it heavily but this doesn’t seem to be the case? Latest release was just a month ago and their github repo is active.

Jellyfin/Plex like many have mentioned.

I personally like Syncthing for petty much everything else. For general file syncing of course. But also with Joplin pointed to a synced directory for notes. With keepass as a password vault. With synced config directories for some apps across devices like newsboat for RSS, and neomutt for email. I also used to use it with rtorrent via a watch directory, though I currently am using a seedbox for that purpose.

VPN (openvpn/wireguard) is a good idea if you want to access your services outside your local network, without exposing them all globally.

My suggestion just changes your threat model, so may not be a good one based on your wants.

Perhaps consolidate systems? Managing less devices = less points of failure. But adds the risk of any given failure being more severe.