Don't get Vista now, because there are bunch of bugs with that operating system. It's too early for it right now. You should stick with Windows XP. Don't get Windows XP Home Edition, get the OEM copy of Windows XP Professional since its a lot better.
64 Bit, I would say get Windows XP Professional x64 bit, because you will have the flexibility of enjoying a 64 Bit operating system, PLUS your computer would be faster than if you get Windows Vista.
If your son wants to play Halo 2 or other games which require Windows Vista, then I suggest you get the Windows Vista Ulitmate 64 Bit operating system or maybe even Home Premium or Business, but like I said, Windows Vista has bugs which leads to incompatibility, so I would stick with Windows XP.
I think John you should tell your son to test out Windows Vista and try it out to see how it works before you buy the operating system, because Vista allows you to try the copy for 14 days free, even the most expensive edition, but again, I can't gurrantee any compatibility issues and XP has been out there a lot longer, so I suggest with your memory and stuff to get Windows XP Professional x64 Bit Edition. For even better compatibility, getting the 32 bit instead of Windows XP Professional would be better and that is the one I have right now on my advanced gaming computer.
OEM and Retail: OEM ships with just the operating system CD and the licence. Retail ships with the CD, the licence and the books and stuff you would expect from a software box, however, Retails are like double the price of the OEM and that is why it would be better to get the OEM. Oh, another thing I need to stress here, OEM doesn't have support for the operating system like the Retail does and if you need support for the operating system, you are going to need to get the retail.
The pros of 32 and 64 bit again is compatibility issues, despite on your hardware, you might find a certain device on your computer not compatible with a 64 bit operating system, but since your computer is brand new, I really don't think you would have any problem with compatibility. 64 Bit technology is more advanced than the 32 bit and newer processors come with it.
I would say Dual-Boot (if u have enough money to afford both):
1. Windows XP Professional 32 bit.
2. Windows Vista Ultimate or Home Premium 64 Bit.
Or test one of them including Windows XP Professional x64 bit edition to see what you like the best and use just one of them.
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