I am constantly amazed at the number of bugs and seemingly obvious UI issues pervasive throughout microsoft products. It feels like their product philosophy is "jack of all trades, master of none" - they try to support so many uses cases that there isn't a cohesive best practice anywhere.
I feel like this has only really been the case since about 2015, so instead of ascribing it to a "jack of all trades" philosophy I believe it can be more readily explained by a "lets hire a bunch of webdevs to work on our desktop OS" philosophy.