Even before the more recent enshittification, Windows has long suffered from prioritization of corporate/enterprise needs over those of end users, rendering various parts of the system more complicated than they need to be. This is visible going back to 3.x/9x; the versions of Mac OS (and BeOS) of the same vintage are more friendly and approachable on several fronts.

Yep, I used 3.x and Tabworks. Mac also had a habit of crashing and inopportune times in that era. BeOS, though, was in a league of its own...