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At work on the server side we still have a few legacy companies that use NT 4, can't wait for those to go away. At home the oldest is Vista, despite being considered a horrible OS it suits my needs perfectly. Never crashed, no problems but I do prefer 7 so may upgrade pretty soon.
My uncle had a 98 desktop that whenever he needed help I dreaded it. Luckily he finally upgraded and got a new desktop w/7 and loves it. Everytime he put a DVD in the 98 desktop the resolution would kick back to 640 x 480 VGA mode and needed to be fixed plus a number of other stupid issues that we are both glad are gone.
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