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Yup, it seems a side effect of data driven approach is that Windows no longer cares about its own reputation.

Expertise-driven design did not give us any Windows operating system. I don't believe that MS Windows is the kind of system OS experts would design.

But - perhaps you're referring to the user interface? Or just the kernel? Or the driver mechanism?

Define "people". Tech people, people/customers in general, some other group such as shareholders? Both your point and the point your responding to could be true at the same time both anecdotally and/or in the data. Anecdotes are probably just another form of "expert opinions"

It's entirely an anecdote, but from my experience, Win7 was broadly accepted as a good iteration among techies and non-techies both.

As a software engineer, I actually find a lot more to be excited about in Win10+ thanks to WSL and other such things. But I don't hear my acquaintances who are non-techies being positive about anything from Win8 on.