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Steam has now officially stopped supporting Windows 7, Windows 8, and Windows 8.1.
(www.theverge.com)
This is a most excellent place for technology news and articles.
Yeah, I've used windows from prior to 3 (when it was more of a shell to navigate DOS apps) to 3.11, 95, 98, 98 SE, ME, XP, XP SP2, Vista, 7, 8, and 10 (and probably NT via school). The only ones I'd describe as awful are the < 3 version (mostly because I was already using 95 at the time), 95 (unstable mess), ME (even more unstable mess), and 8 (UI screamed "we need to make our OS more appealing for the tablet market"). Vista might be the one I spent the most time on, now that I think of it.
Are you a masochist?