This started with Compaq in 1984, and has followed through to today. Microsoft has already paid lip service to the goal of simplification, but it will have to reinvent itself to deliver. Its approach to software design and its business model rely on making every promising new technology a standard part of Windows. That, in turn, gives Windows one byte of code for every particle in the universe. No one can encompass everything and keep it simple.
Simplicity requires leaving things out.
Simplifying Windows requires Microsoft to loosen its grip. He gets that right on the nose. Microsoft doesn't do that. They scare people into needing every feature, and then the little guys can't keep up. It just isn't in their nature.