In theory it’d be possible to make a Jellyfin UWP app, of course nobody’s made one yet. Maybe it could be you ;)

For Tailscale you just have to install it, start the service, and log in. If you want to install it on just one server and have it act as a gateway to the rest of your network, you can use subnet routers.

It’s a mesh network unlike plain Wireguard, and it’s much easier to set up (with the caveat that there’s a third party involved to coordinate connections and stuff)