>Why do you think Windows is currently such a mess?

There have been some writings and posts here about Microsoft. Here is one from last spring, from a guy that was long time Windows core developer and moved to Azure group. It's well worth reading, what he writes about challenges they have had and most likely still have if not even worse now.

https://isolveproblems.substack.com/p/how-microsoft-vaporize...

and the related HN thread

https://news.ycombinator.com/item?id=47616242

And from what I've understood old chaps like Dave Cutler are involved much less than they were for a very long time.