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You don't actually need to do reverse proxy while using tailscale. You can just use ports as if you're on a local network.
The price is super low, but it's been very reliable. Will highly recommend. You can see their current offers here.
This is the bit I find confusing. Doesn't Plex need that port to be open to the outside world?
Or is your setup only open to devices on your private tailscale network and therefore seeing it as local?
If that's the case, I'll need to see if tailscale can work with osmc, since that's what I have running on my raspi behind my tv
For tailscale/wireguard, you just need to open the port in your machine as if you're using it locally. No need to forward port in your router. For all intents and purposes, you can treat all devices in your tailscale network as if they were local devices.