Man, I would have hated having to switch to windows, especially back then. I still prefer Mac, but the windows of today is far more tolerable.
Back then MS had Windows NT, which was a much better OS than Mac OS of the time. Remember, OSX didn't come out until several years later and the old Mac OS was a cooperative-multitasking OS with no memory protection or separation where you had to explicitly allocate memory to each application. Reboots were de rigueur several times a day. I remember those days well and I think many remember Mac OS as a better OS than it actually was.
I'll agree that Mac OS was generally better than the consumer versions of Windows (Windows 95, 98, and ME), but it was not as good as NT.
Well there are two layers to the issue, really: the user interface and the software architecture. From a UI standpoint, I’ve always preferred Mac to Windows. NT and the DOS-based Windows shared the same UI I didn’t like. That alone was enough to keep me off Windows.
From an architecture standpoint, there’s absolutely no question that among classic Mac OS, DOS-based Windows, and Windows NT, it was Windows NT that had the best architecture. By a wide margin. Had NT not had to support the myriad hardware configurations possible in the windows world, it would likely have avoided most of the (comparatively few) crashes it did have.
I still remember classic Mac OS fondly, as there are still some aspects of its UI that I consider to be better thought-out than in any OS before or since, including today’s macOS. As for stability... I mean, I was able to get it to work pretty well. But other than in carefully curated server configurations, it was categorically impossible to achieve truly long uptimes with it. Certainly not multiple crashes per day if configured decently, but not the weeks or months of uptime easily achieved with Mac OS X or NT. I routinely kept it up for perhaps a week at a time, using sleep instead of shutdown.
But allocating memory manually, and having to configure system extensions to load in the right order to get them to play nice... that I don’t miss at all!!! (I used to do that for a living, in fact: I worked as an on-site Mac consultant back in 2001-02, and did it a little bit on the side for a few years after that.)
DOS-based Windows was much like classic Mac OS in that a carefully tuned system could work well, but any misbehaving program could freeze it up.
Oh yeah, one thing I can say with confidence after working as a Mac tech during the classic Mac OS era: the choice of hardware made a huge difference in stability. While pretty much everything from the Power Mac G3 (mid 1997) on was stable if configured halfway decently, man were there differences before. Some architectures, like the 75/85/9500 series, were great. Others, like the 52/6200 series, were awful. I was not impressed by the stability of any PPC603/603e system Apple ever made. I suspect part of it may have been that the low end systems in the early-mid 90s used IDE instead of SCSI, and at the time, Apple was far, far more experienced with SCSI at that time. By the late 90s Apple had figured out IDE properly and was able to use it on pro hardware, too.