Any idea if you can "tunnel" to a proper public IP which is static? I recently did some digging and realized you can pay to get "reserved egress IP's" on cloudflare, curious if this would work for this?
I am not sure regarding that specific case. I can tell you this: You need a domain name with DNS setup to point at cloudflare for the tunnels to work. The domains can be at namecheap, DO, or anywhere where you can modify the DNS provider tags. At least one machine needs to run the tunneling service. I believe it should be the host that will serve the traffic.
Yes. I serve my websites from my home network over a reverse ssh connection to a vps. I only need the vps for it's static ip. Not that fast, but my sites are small. There are open source solutions for this as well.
Interesting, are you just using a passthrough proxy like squid? I've encountered issues routing ssh connections through the proxy.