Apple's marketing in the mid-to-late 90's was poor to nonexistent, frankly, while on a technical level Macs weren't any worse than PC's (both crashed a lot and came with fairly comparable hardware, but the Mac OS 7/8/9 UI was very arguably better than the Windows 95/98 UI). Apple's user loyalty was fantastic (and fanatic) in the mid-to-late 90's, but the company itself didn't do anywhere near the kind of promotion they did once Jobs returned.
Yes, Mac OS 9 had technical disadvantages compared to Windows NT and Windows 2000, and Apple had a second-system effect of legendary proportions with Copland. 90's Apple wasn't that great at technology. But they were abysmal at marketing, while Microsoft were fantastic at it.
Apple had overall high product quality but their focus was lacking and they weren't terribly ballsy. They had a distinct feeling of running on the fumes of the Mac's initial success. But it was (and is) a sufficiently great product that those fumes informed an OS that, from a user perspective, remained the best. Mac OS got long in the tooth, but I'd still take it over Win95/98/NT any day.
Both windows (95/98) and macs had their share of shortcomings, you just had to pick, which set you can tolerate.
I think when engineering types hear the word "marketing", they immediately take it as dismissive. But Apple is an example of a company who owes their skin to phenomenal marketing over the long term.