I have found that a Windows 9x to Windows 2000/XP upgrade is a bad idea. But not a 2000 to XP, as they are based on the same kernal. One main reason a 9x to 2000/XP upgrade is so bad is the differences in the way in which 9x core and NT kernal systems handle the registry. You should be fine with an upgrade from 2000 to XP.
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