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Seems like an easier solution would be to run Tor on the VPS instead of via his home internet connection. Nice to learn about sshuttle though.

I have a VPS specifically setup for a Tor relay, as well. :) We're moving soon and will likely retire the "home" Tor relay.

Not poor yet, but on my way to being there it'd seem.

I'm pretty sure most VPS hosts wouldn't be too happy with that