Microsoft's OS business is a classic "cash cow". It's very big and very profitable, but has limited growth prospects and its revenue is currently growing at only single digit percentage points per year.
Every MBA course teaches that the way to handle a cash cow is to milk as much profits from the users and spend as little money maintaining it as you can get away with. You do this to maximise the amount you have to invest in other, faster growing businesses that will be the future of the company, even if it causes long-term damage to the cash cow.
MS have been milking their OS and Office businesses to fund their cloud and XBox businesses and, so far, it's a textbook example of the strategy succeeding; the cloud already brings in more revenue for MS than Windows and is still growing much faster than it.
The OS features that are getting attention, such as VS Code and WSL are ones that have synergy with the more important businesses and help them sell. Things like fixing the safari park of UI conventions don't have that synergy, so the resources that could improve them go to the other businesses.
The ads and forced sign-ins are also part of this; in the long-term, they'll drive some users away from Windows, but right now, they funnel money and users to places that should matter more to the company in the long-term.
MS aren't listening to Windows feedback - and the internal feedback from people working on the product is usually part of it in these situations -, because what's good for Windows isn't what's good for MS.