On April 3rd my Google news feed was all 2 day old April fools articles and one 2 day old article about a game that was free for the next 24 hours.

Yeah, at that point in time we still thought there was a chance of the shorter but faster to produce half life episode 3.

Hypothetically, if I have tailscale setup, would that be a viable workaround since everything looks local on my tailnet?

When I stream from my plex server it’s a direct connection between my device and the server. The only time it proxies through plex is if your server isn’t directly accessible, like ports are blocked or not forwarded properly.