It's unfortunate as I think that era was a great time to be a Mac user. My first PowerPC system was a 6100/60 (first generation PPC) and then I quickly obtained an 8100/80 (first generation) which I used for quite some time. Mac OS was and, IMO, is the best OS I've ever used hands down...at least from a usability perspective. From a technical perspective it was nothing to write home about. Manual memory allocations, lack of protected memory, lack of PMT all made for a system which could easily be taken down. But surprisingly was reasonably stable. Enough so to make the Macintosh my primary system for many years as that "other" OS was very unstable.
I didn't become a "Mac guy" until 2012 when a cheap laptop nearly cost me a degree. I finished(and passed) the presentation I was giving on a borrowed aluminum MacBook, then bought my own 13" MBP the next day.
In any case, I think both OSs have had their ups and downs but on the whole both have evolved into(relatively) stable systems.
I can remember the days of Windows 95/98 and getting a BSOD every other day. With both OS X and Windows (for the rare occasion that I use it) you can pretty well count on it staying stable and only rarely giving you issues.
I'm just sorry that I never learned the classic OS in its "glory days." Even so, I'm often taken(pleasantly) by surprise at the way things "just work" in it. As an example, when I first started seeing disk images in Windows I had a hard time wrapping my head around them, and even at that didn't know what really to do with them. By contrast, I can boot up System 6 and mount a floppy image. By the time OS 9 came around, a .smi image would automatically mount by just double clicking on it. I would have never imagined doing that 15 years ago.