What made system 7 and 8 worse in some respect was when it crashed, it crashed hard without warning
With windows the crash was progressive so you have time to save and prepare.
I also have fond memories of windows 2000. It was rock steady and polished. I preferred it over system 8 and even OS X which had to many Unix conventions.
I once proved to my boss that a font was crashing System 7. And we always unplugged the network when we didn’t need it because a crash on one Mac could bring down every other Mac on the network.
With System 7 or Mac OS 8/8.5/9, if one used it for long enough with a stable software setup you'd eventually get a gut feel for what programs, extension sets, etc were most likely to invite a crash (it wasn't a terrible idea to reboot after a long web browsing session with Netscape for instance). It wasn't surefire, but one could get it into a somewhat stable state. You never stopped hammering ⌘S, though.
Windows 2000 was incredible. Running it after having wrestled with 98SE was like getting teleported from a garbage dump to sunny meadow with a fresh ocean breeze. I've never seen machines transform quite as radically as they did when upgrading from something earlier to 2000.