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had:
MSDOS (dunno which version)
Win95
Win98
Win98SE
WinXP
Vista
used:
WinME (motherboard died below it after 10 minutes to the install so I couldn't mess with it much)
Win2000 (on school comps)
WinXP is the one I prefer right now. I would use Vista if its UI inventions wouldnt be retarded - it's painfully difficult to even browse my computer, not even mentioning the labyrinth that the Control Panel became.
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