I think I meant whatever came after WinXP which I recall was the last solid version. Either way, I sort of switched to Linux in those years and never looked back again...
Not really. They started doing the "easy-to-use" alternative configuration panels in Vista. Windows Vista also started requiring driver signatures, making it impossible to write your own device drivers without going into the ugly test mode on every boot.
Windows XP was the pinnacle, with everything working just as it should.
(yes, hardly anybody remembers that there was a Windows version between 7 and 10 - but it did exist, I'm not making it up, saw it with me own eyes on a coworker's PC once).
Considering Windows 7 (if you count ESM) was supported all the way up to 2020, it's no wonder people skipped 8 (start menu tiles aside). It was a weird release schedule, and it was split into two versions 8 and 8.1, with 8 only having like 3 years of main stream support, and no ESM and 10 released just two years after 8.1.
If you count paying for ESM, someone could have gone from XP->7->11 and still been within support the whole time. Or from vista straight to 10.
Fun fact: Windows for Workgroups 3.11 was supported all the way to 2008. I believe it was the longest supported version of Windows.