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I ran Windows98SE until recently. In general I didn't have many problems with it, but it did have problems dealing with plug-in USB devices.
Our office upgraded to WinXP about 15 months ago so I've gotten used to it. I upgraded my home computer to it early this summer. I don't have any problems with XP but find it slower than 98 plus it requires more hardware to run, but it does deal with USB devices pretty well, such as my camera card reader and my Axim. We upgraded at work because the design software we use requires it. I upgraded at home because of my camera software.
Regarding Vista, I would not get in a hurry to upgrade until I had to due to software compatibility. I'm skeptical that it will be a big improvement over XP.
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