I’m not a plex/jellyfin user, but I have a server and did try setting up Wireguard (as well as headscale). Could not get either of them to work. I use containers pretty often, so no issues there, but debugging networking issues is just above my pay grade. Tailscale just worked in like 5 clicks. It was stupid easy. If the alternatives get any easier to use, I would love to switch over to FOSS.