If you switch that metric from good/bad instead of success/failure, it makes more sense. Something doesn't have to have been objectively good to be sucessful.

Here's how I remember it:

3.1 was the first windows GUI for mass consumption, and was successful, and pretty decent for it's time.

95 was also succesful, but I remember it being very, terribly unstable. Moreso than 3.1.. i put it in the bad column based on that.

98 improved on this and added a lot. Good.

ME was utter dogshit.

Kernels changed from ME to XP, so I make the link there. Microsoft did provide a direct upgrade path from ME to XP.

XP was awesome

Vista was horrid.

7 was awesome

Now 8. If they continue the pattern, 8 will suck.

It seems like there's a micro pattern like "new UI paradigm" >> "polish and improve new UI". 98 improved on 95, 7 improved on vista, XP improved on 2K.

We're talking about Microsoft here! What about DOS?

I was talking about Windows, actually. I do remember some versions of MS-DOS being marginally better than others, but I don't think it had any predictable cadence.