Windows was such a huge pain back in those days, while MacOS (which wasn't really called that at the time) blew it out of the water, particularly when it came to multitasking.
Of course, MacOS sat still for years, lacking protected memory or pre-emptive multitasking until they scrapped the whole thing and replaced it with NeXTSTEP to produce OS X, so Windows eventually caught up and then surpassed it. I had enough issues with Win95/98 and the DOS legacy to say that Windows probably didn't catch up (with a consumer OS) until Win2K, which surpassed MacOS, and that ruled the roost for a few years. OS X didn't come out until over a year later, and the early versions of that were super rough.
But once they all evolved to a certain point, I think that the operating system mattered a lot less. They all got good enough that the users don't have to care about the low-level features, and there are utilities to tweak them any way you like, so it's really just down to personal preference at this point. You're going to run most of the same software no matter what OS you pick, and operating systems are increasingly just "the software that runs your web browser".