Same ones I'd pick out as the "bad" releases, as someone using Windows since 3.1. 10's kinda a dud, too, though. If 7 supported newer hardware (or, vice versa, rather) I'd still be on that. 10's got WSL2 and... not much else going for it, and even that's not really a normal-user feature.
Same, and DOS before it. I've always been a Microsoft fan, but I'm a bit tired now. Apple silicon is a killer feature and I'm finding it hard to justify not moving wholesale to it (I'm dual wielding right now).
I do feel like MacOS has done a better job of continuity - they change the system preference tool one time, Microsoft has done it like 4 times. Microsoft messed with the Start menu nearly every release, most people would still be fine with how it was way back in XP/2000. The place where MS shined was program and api compatibility and no sudden surprises (usually) - you knew what was coming down the roadmap ahead of time!