I think the NT4/2000 desktop was pretty perfect. It laid down everything without getting in your way. A lot of early systems were forced to follow simplicity because of lack of resources. This coincidentally led to better interfaces because complexity is difficult to get right and often is in service of business interests instead of technical interests.
I think its obvious that there's a degradation in business products as they age. They become more 'competitive' which means more profit-seeking, so the marketing end of things takes over and the engineering end takes a back seat. Simplicity is replaced with shiny and complexity to catch more edge case sales. Weird cargo cults emerge, product manager cults of personality, etc instead of following proper usability guidelines. Industry fads become self-fulfilling prophecies. Lockdowns and walled gardens emerge because they are more profitable than open systems.
Today, I almost can't believe how hostile and bloaty Windows 11 is and MacOS isn't much better. At least we have FOSS, but the commercial end of things is 'late stage' and frankly awful.
There's a real tragedy how capitalism always leads here. I sometimes wonder if the USSR stuck around what a more technocratic-led system would produce compared to the West.