I started with MS-DOS, installed Windows 3.1, and have upgraded all the way to XP. For each hardware upgrade, I clone the hard drive. It works, that's my computer. Windows ME required some tweeks to make it stable, but I did it. I never did use Windows 2000: MS-DOS -> 3.1 -> 95 -> OSR2 -> 98SE -> ME -> XP.
Rob Dyck