I don't disagree with you on the being run by humans and having inertia aspects. I just think you're underestimating how damaging trying to force known data leaks and uncontrolled software into a large organisation would be.
The data leak aspect is a concern for the lawyers, as well as the obvious underlying security implications. I'm only involved with smaller businesses, which previously used Pro versions of Windows, but even we don't seem to be able to move to Windows 10 without risking violating various data protection laws, NDAs, and so on. What happens to larger businesses, particularly those who work in regulated industries and who really do get audited from time to time, if Windows 10 Enterprise imposes the same vulnerability?
The forced upgrades also have obvious stability and reliability implications. Microsoft has long provided tools for corporate system administrators to manage large numbers of Windows desktops and deploy updates (or not) according to their own schedules and testing requirements. I have never encountered a large organisation using Windows whose administrators do not use these tools, and the answer to many problems with Windows updates for these organisations has essentially been "If it took out the 10 dummy PCs in the test lab, don't deploy it to the rest of the organisation". Again, if Windows 10 Enterprise took away that flexibility and allowed (or required) users to start upgrading their own systems, I can't imagine corporate IT tolerating that at all.
In short, it doesn't necessarily take an incredible amount of silly things to tip the balance. Even one or two things will still do it, if those things are silly enough.