I'm someone who stuck with Windows 7. The history of Windows has been so shaky, and the general software quality of Microsoft is so low, that the only rational strategy with Windows is "if it ain't broken, don't fix it."
I have both Windows and Mac hardware, and I prefer to update my Mac OS as soon as updates are available. On reflection, I suppose it's because the software quality is always high, and I know the core linux-based OS won't have any major changes. Upgrading, except for the occasional "I guess networking doesn't work now," is a pleasant and expected process. There are also rarely, at least for me, compatibility issues with existing software and newer Mac OS versions.
It seems like major versions of Windows are completely different operating systems, with "improvements" built on top of original hacks and poor code, and news reports of zero day crippling flaws in every new version. And of course, Windows 10 looks visually terrible. Flat design in general looks bad, but Windows 10 seems to have done something especially colorblind with it.