When I first got into self-hosting I started out using Tailscale, at that point i didn't know better and figured it was all or nothing. It has actually worked flawlessly to be fair. Probably not the best or smartest decision of my life. But am now slowly wanting to turn to just a clean WireGuard setup.
I have everything connected over Tailscale, and strictly only use IPs delegated through this system. So i realise now that I have to step away from that if I want to make it work locally :P
It probably does tbh, I'll have to check the documentation to double-check though. Anything that isn't foss tends to get a handful indeed; Jellyfin genuinely is a better experience than Plex imo.
Totally agree with the mentions of Wireguard and Tailscale. They make this super easy. Have done exactly this myself before, for the same use case.
However at the time, i had to change something in the server-properties config file in order for it to work properly. Minecraft servers still authenticate users when hosting yourself (afaik). This however isnt possible over a mesh netowrk like wireguard/tailscale. I simply had to change a boolean value of the line called something like, server-online, or online-mode..
This feels like it would be the design of the Escobar phones (the golden scam phones).