The work that you need to do in order to unwind from legacy Windows stuff like fat apps, IE-optimized websites, and legacy Office-based workflows makes it pretty easy to move to an iPad to Google, etc. The only thing that Microsoft has going for them is that every other vendor is also fucking up client computing in different ways.
I haven't seen any issues with apps though, so I have to dispute this claim. We just moved 5,000 employees from Windows 7 to 10, and it went far smoother than anyone really expected - everything just works. It's a wide range of apps too, everything from in-house WPF apps to CAD and engineering software.
IE11 support will go away at some point. Many of those apps are now being updated to work on Chrome -- I know of a few large shops that aren't testing IE or Edge anymore for internal apps!
I do agree that they did a heroic effort on making the update process incredibly reliable. Most non-prehistoric applications transition seamlessly.
Note that I personally equate Windows 10 and the subscription "Office 365 ProPlus". The layers of complexity are astounding. I present to you what I call the "Office 365 ProPlus Build Decoder Ring" - https://support.office.com/en-us/article/Version-and-build-n...
Windows 10 itself has about 8-10 releases that an enterprise needs to think about. Transition from release to release has gotchas and additional Windows-Office gotchas. (For example, the way Office authenticates changes in certain builds) (See: https://www.microsoft.com/en-us/itpro/windows-10/release-inf...)