Ask him if he's really sure he wants Ultimate.
Most people don't need all of the features of Ultimate and can save money by looking at other versions.
OEM is the cheapest, however if he upgrades his motherboard in the future then the license agreement does say he needs to buy a new license.
Retail Upgrade would allow him to move his installation from machine to machine.
Oh and Vista is very much an upgrade from XP - don't listen to anyone who tells you any differently.
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