Especially if the company that develops the os in question shows a track like this one: https://cve.mitre.org/cgi-bin/cvekey.cgi?keyword=microsoft+w.... (Security)
I also wonder how long it will take before the shiny new anti-piracy instruments will be abused by a member of the intelligence community, a low-level politician or perhaps embedded into desktop OSes. http://pimg-fpiw.uspto.gov/fdd/50/148/096/0.pdf (You are not the owner of your files)
It's always easy to accuse the user rather than who exploited the vulnerability in the first place or who does not backport security patches when users obviously do not like the new versions of a software. - https://www.netmarketshare.com/operating-system-market-share... - https://www.extremetech.com/computing/227693-windows-drops-b...
Frankly speaking, Microsoft has gone too far into abuse, lock-ins and presumptions.
As a personal comment, I have an old Windows 7 laptop I use with some win32 software, I do not have the slightest intention of upgrading to Windows 10 (not for laziness or hubris, but because IMO the product is not worth the price). And if it was a critical system, than Microsoft Windows would not really be considered among the options.