Its not difficult for technical people like you or me, but my friend who just wants to watch their favorite show on my Plex on their TV won’t know how to traffic engineer the traffic over a Tailscale network to my network. My mom won’t be installing Tailscale on her laptop and phone.

With Plex, you’re getting the easy ability to grant access to users. You get a single pane that can search across multiple Plex instances, and NAT traversal/port forwarding. Jellyfin makes you figure that out yourself.