Perhaps we have positive memories* about Win2k (NT 5) because Microsoft killed it off before there was time to release a lousy update.
Or maybe there was a lousy update, Windows XP RTM (NT 5.1), which upset almost everyone at the time. Whilst attempting to maintain compatibility with Windows 98, MS created a monster that offended those who wanted ease of use and those who wanted security. Windows XP SP2 was such a major rewrite that it deserved a new NT version number -- but that would have annoyed the marketing people.
XP SP2 was a reputation changer for Microsoft. The company had to change its products and they tried to show it in a big way. Following the Vista debacle. MS created Windows 7, a version that most businesses and consumers wanted to adopt.
Somehow, I don't think that Microsoft perceive Windows 10 in the same way as Windows 7 or XP SP2. They are still fiddling around, not having learned the lessons from Windows 8/8.1.
* I occasionally wear my Win2k Rapid Deployment Program (sic) polo shirt.