Setting up a SSH tunnel would be relatively easy, though it requires a bit of knowledge about setting up servers and such. A friend of mine did this in school, and it worked quite well, though it was mainly for remote controlling his server at home (he's the owner of smwcentral, a fairly big website, so being able to remotely control the server is practical).
The biggest blockade to doing all this though, would be that your upload rate is basically shit, which means your speed in school will be shit too when you proxy.