Me was just a buggy piece of trash, maybe it would have gotten fixed, but XP was around the corner. Speaking purely from personal experience—had a desktop running Me, it’s the only time I ever saw Explorer crash.
Vista’s actually a decent Windows. The changes to security that broke a bunch of apps and made pop-ups everywhere stuck around, they just got polished a bit in later Windows, it would have been fine if Vista had a longer life.
Windows 8 had the Metro UI and introduced a ton of misguided changes around the assumption that people will be using touch—changes which were often half-implemented at best, so even if you had a touchscreen (I developed for these), you had to constantly switch between the Metro and desktop interfaces. A lot of those changes got unwound in 8.1 and 10.
IMO the bad ones are Me and 8. Anything that fixed 8’s problems would have gotten a new version number.