[jonhohle]

I know this is internet canon, but is questionable, in my experience.

   x DOS - passable
   o Windows 1 - bad
   o Windows 2 - bad
   x Windows 3.1x - good
   x Windows NT 3.5 - good
   x Windows 95 - good
   x Windows NT 4 - good
   x Windows 98 - better
   x Windows 2000 - great
   o Windows ME - bad
   x Windows XP - better than 9x/ME, on par with 2000, eventually long in the tooth and outdated
   o Windows Vista - bad
   x Windows 7 - good
   o Windows 8 - bad
   o Windows 10 - ???

The NT lineage was reasonably good prior to Vista (in the context of that OS family). The DOS lineage was reasonable good until ME (again, in the context of that OS family).

XP was a significant improvement over the DOS lineage, however, Microsoft had a reasonably good run in the 90s and early 00s.

[Karunamon]

I'd include the point releases in that. XP once it was patched was awesome, but I recall nothing but problems prior to SP1-2. There's also 8.1, which fixed a lot of people's W8 complaints.

[MikusR]

And Windows 8.1 Update 1

[ytdht]

I pretty much agree with you except for the fact that NT3.5 and NT4 should not be included in this list because they were not consumer versions... and I would rate DOS as good. Also, I am not sure if 8.1 should be considered a major as I never used it.

[seba_dos1]

As far as I remember, Windows 98 was rather considered bad until Windows 98 SE came out.

If you include Windows 3.1x, then why not 3.0? Also if there's NT 3.5, then why not NT 3.1 and NT 3.51?

[rjsw]

There was Windows NT 3.1 too, I don't remember it being all that bad.

[ytdht]

if you are going to include Windows NT, you should probably also include Windows Phone OS