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Hardware drivers are going to be your biggest problem. If you have any old printers, scanners, or other office equipment make sure they have the drivers.
Although Vista has received a bad rap in the tech press and blogs you shouldn't discount it. Especially if you're looking at a 64-bit setup, Vista is going to have better support for hardware and software. I've been running 64-bit Vista on my primary machine for quite a while now, and it's been rock solid in terms of performance. I didn't run into any major software issues, but did have some issues with hardware drivers.