Apple's products weren't highly regarded through most of the 90s. The survived on a niche market at the time, but weren't highly regarded during this phase either for their design or technical architecture. Pricing wasn't their problem -- their products were the problem.
It wasn't until 2000 or so when they got their mojo back.
They were highly regarded in their niches. If you needed a computer to edit photos or to assemble a print publication, a Mac would be your obvious choice. In the PowePC era, it was the fastest computer you could buy that ran off-th-shelf productivity software and many found their way into labs as instrument controllers. Considering the size of their lineup, a couple lemons (pun intended) were to be expected. Still, considering how many models were made, I saw more bad computers coming from PC makers.
And, until the arrival of NT4, PC GUIs had little to no advantage over what Apple was offering. Windows was ugly and crash-prone. In retrospect, NT4 was also very crash prone, probably because MS moved graphics drivers onto kernel space. Windows only became more acceptable (some would prefer "less offensive") visually with the NeXT-like visuals of 95.
That's not the history as I remember it. Windows 95 came before NT4, and it was the first to introduce the famous "start button" visuals. 95 however was still based on the old kernel and it crashed a lot. NT4 came later, with the same visuals, but due to the NT kernel it was remarkably stable.
Windows NT4 was much more stable than the previous Win3.11->95->98->Me line, but - primarily due to moving Graphics drives into the kernel for performance - was considerably less stable than its immediate predecessor in the NT line, Windows NT 3.51.
While 95 introduced long filenames to a mainstream audience, it was very unstable. MacOS 7.5 was not perfect (and the PPC migration brought some instability), but it was not nearly as bad as 95. NT4 had a kernel internally more advanced than MacOS classic, but most users wouldn't be able to tell.
Microsoft's GUI offerings started to really compete with Apple's with 95 and matured through NT4 and 2000.
Apple had a good product, if you compare it with what the PC market was offering. OS8 and 9 were well-rounded OSs that competed mostly against the 9x family, as XP, which made the NT kernel mainstream, wasn't launched until after OSX.
Apple's products were always highly regarded. Their problem was pricing - they charged too much for boxes Dell sold for much less.