Windows 7 is much, much better.
You go right ahead. I buy video games because I want to play them, not because I want to make them and then play them. If I wanted to do that, I'd still be collecting Lego sets.
God help the internet helpdesk people who have to walk 67-year old customers through command line FTP in Windows 7 to get their sparkly new computer online, and the retail people who get yelled at because the computers they sold "don't work", etc.
Personally if I didn't already have a perfectly-working PSP-2000 I'd be keeping the PSP Go in mind.
That said, taking some things like composition or entry-level mathematics tends to be the same regardless of whether you take it at a community college for $40/hour or at a university for $200/hour. Some of the stuff the kid took won't be worth anything anywhere, but he'll have a good chunk of his general education requirements knocked out at whatever university he gets into.
Well he is paying to live in the dorm, so what's your point?
Having a Windows-only policy on campus is an insanely shortsighted thing to do, given the number of students using Macbooks and the presence of UNIX-type environments in computer science departments. I'd wager if you just told them you run Linux you'd get a pass.