I have several services on my home server, most of which I access using Tailscale, and it works great. I had a couple services on Cloudflare tunnels in order to access them from devices that I can’t put Tailscale on.

Plex is going to start charging for remote access. So I figured now would be the time to migrate to Jellyfin. But using Jellyfin on Cloudflare tunnels is against their TOS. I have a Roku TV at a remote location that I use to watch Plex. I won’t be able to do that anymore. And I can’t put Tailscale on it to serve Jellyfin that way.

I was going to set up Nginx Proxy Manager to use my domain name for Jellyfin so I didn’t have to use Cloudflare tunnels. But in setting that up I found out that my ISP is double NATting me, and I haven’t been able to find a way around it.

So I’m left with two options: 1) buy Plex Pass so I can continue to stream remotely; or 2) get a VPS, run Tailscale and NPM on it and switch to Jellyfin.

I’m looking for a sanity check to make sure the VPS thing would work the way I think it would. If it’s running Tailscale then the double NAT would be a non-issue, correct? Is there another option that I haven’t thought of yet? Which of the two options would you choose?