Ask HN: Should I bypass my Colleges Oppressive Software?

I wouldn't try to circumvent their policies.

Get your own laptop for your studies, and just use the college's computers other than for sending in completed work.

If I were in your shoes, I would ask for my money back and then go to a college that respects me. It would be a huge hassle I am sure, but security, privacy, and freedom are worth it.

I'm assuming you agreed to use their hardware. They have the right to do what they want with it. If you don't want to follow those policies, don't use their hardware.