There is no pattern, those pictures are just a silly meme and ignore the realities that contradict them.
Here is my personal opinion of various windows versions, and IMO there is no good/bad/good/bad pattern:
Win 3- terrible, just use DOS
Win 3.1- slightly better, but still inferior to DOS, another BAD
Windows 95- Good compared to everything up until this point, but BAD compared to future OS.
Windows 98- Fixed a lot of the issues with 95, but had some problems of it's own, better in Win98 Second Edition.
Windows 2000- Good, amazing, perfect OS. Flawless in every way.
Windows ME- Considered bad, but IMO pretty much equal to windows 98. Clearly inferior to Windows 2000 though.
Windows XP- At release, BAD- lots of driver issues, some infamous problems with sound blaster live cards and via drivers, but after the 3rd service pack it was mostly redeemed and considered good.
Windows Vista- At release, considered BAD by most, but IMO most of the blame is on bad drivers from nvidia or ATI. After SP1 I had no problems with Vista, although many still consider it bad. Still nothing wrong with it IMO, but 7 makes it obsolete.
Windows 7- Good, considered good by most users.