> They went from 95 and XP, some of the best operating systems from a user's perspective

I mean that's some rose-tinted shit if I ever heard it, 95 especially. 98 OSR2 improved quite a bit on the situation, but I don't recall having a great time with 95. It was still a glorified DOS extender in many ways, often slow to start up and shutdown, PC hardware and drivers were a mess and system stability therefore poor. This was right at the beginning of the concept of "PnP" in the PC world (plug and play) and it was a cruel joke most of time.

Windows 2000 being from the NT line was peak Windows in many ways. I resisted XP but it was ok for most people admittedly.