While pre-OSX MacOS had problems, for a long time (at least until Windows95) it was still better than Windows. I worked in a college computer lab through the early 1990s and I could understand and respond to almost any Mac problem that a student had verbally and they'd understand how to fix their problem (unless they were particularly dense) but I couldn't understand or solve a single Windows problem that way. Even if I understood the problem they were describing, I couldn't tell them how to fix it without worrying that they'd mess it up and make things even worse. Basically, the Macs had a handful of common and predictable problems that were easy to fix while the Windows machines could just be messed up in too many ways to keep track of. Of course I pretty much jumped from MacOS to Linux at that point and them jumped back after the iMac, iBook, and OSX.
I worked in a college computer lab through the early 1990s and I could understand and respond to almost any Mac problem that a student had verbally and they'd understand how to fix their problem (unless they were particularly dense) but I couldn't understand or solve a single Windows problem that way.
And I worked in one through the mid 90's and while you may have experienced greater transparency in the Apples of the early 90's by the time windows95 came out that was not enough.