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Pemalite said:

Missing several operating systems in that line... Like Windows NT (Good), Windows 2000 (Good) and Windows 8.1. (Meh)

Windows 95 was also a good OS when it launched, it's issue was that technology was moving rapidly and thus had sketchy support for things like USB, so Windows 98 ended up being defacto extremely quickly.

And Windows XP was marred with a ton of issues upon it's release, it was essentially Windows 2000 with a new skin, lots of old Win9x software just didn't run.

Sad that I am old enough to have used every one of these operating systems while they were in their prime though, haha.

True about XP. It wasn't good until SP2. ME was a nightmare. Hard to say anything about Vista as I skipped it entirely, only tried it with SP2 after Win 7 release and it was actually pretty good by that time. No different from Win 7. Win 7 also was downgraded with SP1 from my experience, lots of problems with Windows Update for some reason, when it just simply doesn't work out of the box.