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Is it really illegal?
Sure, the fine print says you can't, but does that really mean it's illegal. I doubt you'll ever see a software vendor, particularly Microsoft, try to press the issue. A ruling that the First Sale Doctrine nullifies all those non-transferable clauses is one of the last things they'd ever want to see.... probably right up there with a Linux-based OS being sold in the mass market to consumers, who will in turn demand linux or at least wine-level compatibility from third party software.