Whatever you decide on set him up with a backup system of some sort to
backup his classwork. I've been using CrashPlan (www.crashplan.com)
with a subscription to their CrashPlan Central service for a bit over
a year now and it's been a great solution. I've got my wife's laptop
and my own backing up to CrashPlan Central for offsite backup and an
old workstation running at home of on-site backup. Working great and
it's saved us data loss on a couple occasions already. CrashPlan runs
on Windows, OS X, and Linux.

It appears this isn't what you're looking for, but as a heads up for
you and anyone else who may be interested: Apple is running their back
to school sale again this year.
(http://store.apple.com/us/browse/campaigns/back_to_school?mco=MTg2OTQ5OTE)
On top of the education discount ($100-$200 off depending on the
computer) you get a free iPod 8GB Touch (after mail in rebate). On top
of that they usually have a mail-in rebate on a printer as well.

When we got my wife's MacBook two years ago we got the MacBook, free
iPod, and a nice multifunction ink jet printer. We picked a printer
that had copy/print/scan capabilities as the only way we would get
another printer was if it was free (or low cost) and did something we
couldn't do with our current laser printer. It hardly gets used for
color output, but it's been nice to have a copier, scanner, and fax
machine. The printer only cost $20 after the mail in rebate.

The Mac can run VirtualBox (or other virtualization solutions) to run
Windows or Ubutnu, and there's the Boot Camp option as well.

--
Andrew S. Zbikowski | http://andy.zibnet.us
IT Outhouse Blog Thing | http://www.itouthouse.com