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.
Yeah, Apple's 90's marketing was ass. But I loved every last Mac I owned during that decade.
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.
I don't know about you, but the things I do not miss are putting spaces in extension names to reorder them (at boot time, they were loaded alphabetically and there were often conflicts, if the order was "incorrect"), manually setting up, how much RAM can a specific app use, or rebooting with virtual memory on/off, depending on which app I wanted to run. I still remember, that reading websites with table-layouts on the only somewhat standards-compliant browser (IE for Mac) was exercise in frustration.
Both windows (95/98) and macs had their share of shortcomings, you just had to pick, which set you can tolerate.
Windows had the same problem, except instead of having conflicts between extensions (which everyone understood were extensions to the operating system), installing applications could cause conflicts. Personally, I never reordered extension names to avoid conflicts.
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.