32 bit operating systems (such as XP) are limited to 4GB or ram (minus some overhead - usually results in 3-3.5GB), so that extra 2 - 2.5 GB would be wasted. Now there IS a 64 bit version of XP, but it is very unlikely that is the version you have.
Win7 I'm sure you'll be getting the 64 bit version so you'd be golden on RAM with that.
Aces High is natively multi-threaded which means that it WILL take advantage of multiple cores, however with most games (including AH) you're usually better off with a faster dual core over a slower quad core. Of course, YMMV. Believe me, your I7 will be much more than fast enough to handle AH and MSFS X, if you have a decent video card.
I have no experience with gameport devices on Windows 7. I know USB adaptors exist, I just have never played with this at all. If Win 7 flat out won't support it, then that would be your only reason for using XP at all with that system, but I'm sure there's a work-around for this somewhere...