I think Microsoft is definitely gaining in "cool". Every designer (almost universally on Mac) that I know that saw the Surface Studio reveal trailer was smitten. Not sure if that will translate to sales - it's hard when your workflow is completely based on your platform. But everyone definitely thought the machine was amazing.
For Windows though, I don't know. I know OEM partners like Dell/HP/Samsung are building high quality machines, but when I think of old PCs and laptops that I've used, I just picture them as clunky, unpretty plastic machines.
Nope, unless Microsoft listen to changes and recommendations from their loyal users and incorporate it to their development, i believe they take a good jump to compete with Apple current level. I seen many beautiful recommendations and features by fans, they should tend to those too, to make better product and services, which can change the cards in market share