Are you kidding me? As a high school student, I can inform you that even the most computer-illiterate people know about the various proxies used to get to myspace/facebook/whatever they want to get to. Anyone can type in a URL--in fact, when I had my personal server running with a PHProxy, I saw it jump from 3 users a day (certain periods) to almost constant use during the school day, as people passed around the URL.
Funny you mention the SSH proxy: That's what I do now, and it works really well. I track who is doing what, give everyone their own account, AND get 100% of the pages to work. Not only that, but it's substantially harder to set up putty and your browser than it is to just type in a URL.