Why did Windows 95 setup use three operating systems?

Raymond Chens blog and book (The Old New Thing) is an absolute delight! I always had a big respect for how intuitive the Windows 95 GUI is, and reading his description of the thoughts and methods behind its inception, it's no surprise that it became so good. It seems like Microsoft was extremely pragmatic and reasonable in many of their endeavors back then. It's a wonder how it degenerated into the absolute unit of sh*t that is modern Windows (even if the filesystem and kernel is arguably a lot better, everything on top seems to be developed by an army of interns)

Army of interns should about right. I always suspect that Teams is developed by some beginners who are learning Scrum.

But yes, Windows 95 to Windows 2000 were a huge jump in usability. From Windows 8 on and the “Metro” interface they threw it all away.

I think they rotate the interns every year. That will explain the GUI^WUX advances. /s

UI/UX keep getting shittier over time is an industry wide phenomenon not a Google exclusive one. To me everything kinda peaked in late 2000's and has been on a downwards slope ever since the mobile became the dominant platform so everything from desktop PCs to cars had to look and function like a phone.

Perhaps controversial but I think the ability to ship continuously is also a factor. You just have to pass and fix the things with the most complaints after. A holistic view on the general user experience will never make it to the top of a pile now.