My understanding is that cloudflare will block you from doing this if/when they detect you doing it, someone correct me if I’m wrong.

Off the top of my head, would a tailscale funnel work for what you want? Serving Plex to the Internet without port forwarding?

Actually with Plex, I’m not sure you even need to expose it at all. People can reach your server via the Plex app as long as it’s connected to Plex servers, they don’t need to reach the site actually hosted on your hardware

I’m partial to duplicacy, not to be confused with duplicati. Has worked great for me