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Also if I buy a new computer with XP - how long will that last?
Typically MSFT leans on OEMs to stop shipping older OSes a few months after they release a new OS.
When XP shipped I managed to get a few systems from Fujitsu-Siemens which came with both W2k and XP (two sets of OEM CDs) - gave the option of sticking with W2k until the first XP service pack came out, then switching over to XP at no cost.
If I see a similar offer with XP/Vista I'd jump at it.