Using a VPN in reverse: I need a "public" IP address

Reverse SSH tunnels. It looks like this would be very easy to set up. I need to figure it out for windows too. Some googling will help on that…

I assume that each port I need to tunnel would need its own SSH session. Is this right? This would take care of my web server (Ubuntu) and the GitHub web hook to my build server (windows). These would bypass pfsense since the connection would be from the server itself to the linode VM.

How should I take care of VPNing back home? Can pfsense do reverse tunnelling to a wan port?
Pfsense -> SSH(with reverse) -> linode VM

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