Can you share what the final desired goal is? It sounds like your goal is actually to provide your services to Bob securely over the internet, is that a fair description? You mentioned eventually grabbing a domain, how do you feel about publicly exposed services with authentication? For instance, I use authentik in front of Jellyfin and paperless myself for a little extra authentication juice.
Hey, my name is on that probe! Good luck with the solar plunge little dude!