People are naturally reluctant when upgrading Windows, so the update needs to be as painless as possible, given that the OS you already have installed often has still several years of support left from Microsoft. I think that is one of the lessons Apple learnt a long time ago, and that's why its software frequently changes aesthetics, but rarely in functionally (the dock is the same, system settings are mostly the same, and so on). If you stay on the old version, you know things might stop working soon.
It seems to me that since XP Windows has been for some reason engulfed in a nonsensical crusade to change those things that worked so well already. I still consider the Windows 2000 UI as the most refined and easier to use in all of Windows, and everything after that just complicated and messed up the OS without a real vision (the only good improvement in the UI I think was the 7 taskbar). To see what I'm talking about, it's sufficient to see the mess they made with the control panel, which was clear and easy to use in 2000, then became cartoonish and dumb in XP, and then it got partially replaced by Settings in 8 (and the migration is still incomplete to this day).