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Legally you're good if you wipe the old hard drive.
That all depends on whether the version of Windows is OEM or retail. If it's OEM than technically it dies with the machine it was originally installed on. Although lately Windows has been pretty slack enforcing that rule.
Good point, and very true. I haven't seen it ever really enforced for an end-user though, just business licenses. Generally as long as you're only using a key on one machine at a time, they don't care too much.
I've had them be a bit of a PITA over it, you do get the occasional helpdesk employee that does everything they can to make reactivating OEM products more difficult than it should be.
I think I've done this a few dozen times and only gotten beyond the automated help desk once, and that was for an Office activation. But it depends on the history of that particular key. If the OP has honestly only activated it once on one machine, I'm sure he'll have no problem. If that key has been around awhile, he might end up talking to a real person.
I don't think the automated system exists anymore, every time I need to reactivate a Microsoft product I get put through to an actual person now. Although I guess it could very well exist in certain regions.