Probably not, but then I have never upgraded from one to another. I always buy a new PC when getting a new OS, simply because the time that passes means that to get the most from the new OS, you need to have the hardware capable of running it (usually).
It just struck me as odd that Windows don't allow for an upgrade, and facilitate another avenue for purchase of new products (64-bit version of XP assumed).
I'm on Vista and I've just passed the 5 year mark with this PC. For me, XP was a flop. Vista, once tweaked, has been pretty damn good (winsxs folder being the only untweakable aspect). I suppose I should plan for Win 7 / 8.
Believe it or not, I'm considering investing in a cheap system to see if I can still get W2K Pro to install on it. I have a batch of older programs with 16-bit installers, and for £200-£300, I could have what would be a super-fast W2K system. If I got 3-5 years out of it, it would be a bit of nostalgia and fun.
Not sure about drivers though.
The only drawback is that for it to be a good setup, I would need a KVM, and the better ones start at £100 plus, which is 30% or more of the system budget. Sigh.