We exclusively use Windows on our user's devices (over 10k devices!) and don't have to support anything else. We end up with problems like those all the time.

• occasionally all installations become blocked no matter what means or which user, requiring reimaging to resolve.
• DisplayPort connections mysteriously failing and requiring reboots of the device and sometimes also the dock or monitor. Sometimes we even have to swap the cable out, even though the cable will continue to work in another setup just fine.
• using a different brand of dock than the ones we have at our hotelling stations and disconnecting for any length of time causes wifi to fail until reboot
• wifi at the office mysteriously stops working as you move around the building, requiring restart

None of our Linux test devices experience any of this.