I've concluded in the past couple of years that large parts of Microsoft as an organization have stopped being able to coherently sell to the end user market, and whatever people in the management that would have in the past noticed this sort of thing and taken steps to correct it have left or moved on to other roles.
Signs of things slipping I've personally noticed in recent years:
- The faulty Microsoft web-based store (do they expect developers whose first experience with Microsoft is a web site that can't even sell a Windows upgrade are going to turn around and want to build things on ASP.net?)
- Contradictory descriptions of the different Windows SKUs (with respect to use as upgrades, new machine installs, usability by end users vs. system integrators, etc.)
- Software with seriously flakiness in features that worked in previous versions (e.g. Windows 10 Start Menu search and keyboard navigation), with broken help links, without an integrated installer (e.g. Lync, Sharepoint)