I did a nasty hack a little like this when I was in college. College wired internet had all sorts of filters on it, I can't remember the details exactly. The important thing was it didn't allow the upd ports for counter strike from the wired connection we had in a society room. The computer science department had their own web proxy, which was only accessible from inside their network. Cs students could SSH into special lab machines running linux, which were on the cs network. Crucially, you could connect to them from the general college network, not just another cs network ip. These machines had a series of predictable hostnames, iirc lg12l$hostnumber (lg12 was the labs name). So, the solution was in two parts: first, ssh tunnel to the cs dept proxy, second: connect to openvpn on a vps somewhere using a mode that openvpn has which allows use through a http proxy. This happened on a machine running a dhcp server, which then acted as a nat router for the whole room.

The lab machines I was using were physically accessble to students, who could reboot them, shut then down, whatever. So I wrote a script that would iterate through the hostnames until it found one that it could SSH tunnel through. Mostly it used lg12l0, the first host. One day I got an email from the cs dept sysadmin telling me that lg12l0 was a test host in his office, not a real lab machine, could I please use another one? And no complaints over what I was actually doing with it. I still wonder if he noticed. This setup was running for at least a year, maybe two. Sorry about that mate :D