When I use to dual boot windows I never updated and always "restarted" by just holding the power button down (stupid, yes I know, but it's the only way to reboot it as fast as I'm used to when booted into Linux). Never installed updates and it always worked fine, until I wanted to install updates, then everything broke. I assume this was just caused by waiting too long between updates. My solution was to delete the windows partition and just use a VM.