The issue with Windows is that it's a rolling release. If you've dabbled in Linux for any lenght of time, you'll know that it's best not to run a rolling release bur, rather, a long term stable OS, on any production / mission-critical machine. Rolling releases may be good for general consumption computers (and in the case of Linux they might require manual intervention, so are mostly recommended to enthusiasts, even though distros like Solus execute the rolling release model for all customers well), but they are bound to have some stability issues and random things happening overtime. There is only so much time to put into testing updates in that case.
...And the fact that keeping Windows a rolling release is a dumb idea has proven time and time and time again.
Please, Microsoft, open your LTS branch to everybody. Windows 10 being a rolling release forced me to outsource my more critical work to the LTS branch of Ubuntu, because I simply cannot afford a software update (that is, by the way, forced on me) to get on the bleeding edge Windows to delete all my files.