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Why are they proxying the stream through their server though
Not necessarily. Tailscale uses their own servers in order to do the negotiation, but once the connections are opened on both ends you should be directly connected to each other. All without port forwarding or any config on your end.
https://tailscale.com/blog/how-tailscale-works
Right, but IIRC anyone can go on the plex.tv website and use shared servers due to the "proxy"