According to South Park the movie, Windows 98
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probably 8 or 10
Windows Vista was the start in my eyes. XP (pro) was amazing. And then Vista came out and it broke a lot of things. Security was garbage, applications would constantly lose root files
Vista only lasted 2 years before they went back and turned it into Windows 7 with a few small tweaks, but more or less the exact same thing
98, XP, 7, 10: Good.
ME, Vista, 8, 11: Bad.
It's Star Trek Movies all over again. We just need to hang on for Windows 12.
98 still had plenty of jank, but it was worlds better than 95. I would add 3/3.11 to the "good" list if only because that was basically the only other option for a lot of people and it did what it needed to. I don't recall personally seeing windows 1 or 2.
edit: I guess I could throw NT mostly into the good section, but I mostly just did tech support for it rather than using it.
just after windows 7.