Windows updates used to be seen as upgrades. I remember getting Win95 to run on my 386 with 8MB of RAM (which my buddy said wouldn’t be able to handle it). I was so stoked to have it working because 95 had so many improvements over 3.1. Of course each release had its issues but after some service packs they were usually pretty good.

Maybe it started with Windows ME, but it definitely was in full effect by Vista, where new releases became downgrades. XP was the last great version, when I had to move on from that everything started getting much worse UX-wise.