I think it should be mentioned that during this era, the whole idea of a GUI was still a relatively new concept to most people. It had been less than a decade since the Mac popularized the idea. It's akin to how long it took for cars to standardize on the accelerator, brake and clutch configuration. It didn't happen overnight. When I went to college in the early 90s, most of my fellow students had dedicated word processors or, less commonly, DOS PCs (and one Amiga), as an example of what was the norm. The only reason I used a Mac was that I was in the design program, where Desktop Publishing was experiencing its heyday. But I could never have afforded one.

In 2022, the idea of an average person not understanding what a mouse is for is almost inconceivable. But in 1992-1994 when "Chicago" was being developed? The majority of the planet still hadn't seen one, let alone used one. Discoverability wasn't a nice-to-have, it was paramount to Windows 95's success.

Amazingly, Gates and company realized this and put a ton of effort into UX research as a result. They could have easily dropped the ball transitioning from 3.1's GUI (think Windows 8 as a counter example), so they deserve a lot of credit for getting it right.