I don't think I can give advice on piracy, but I probably can say that OS X does not call home, and the family pack EULA doesn't cover machines that go away to college anyway.

Most (*almost all) Mac users who are aggressively against piracy, the type who freak out when I say I might not have paid for even the tiniest, most ancient bit of software, seem to turn the other cheek at EULAs that restrict you from using software on more than one computer, and will sometimes install the same copy of (for example) Tiger on eleven newworld machines they happen to have sitting around. (true story.)
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