I have a ricoh postscript printer that just won't work on Linux, I also have a Canon 6020 that works well in Linux. The Ricoh works well on Windows. So my experience with CUPS is mixed.

I only need Windows for a few programs, mostly licensed EDA programs that [dumb] companies didn't manage to port to Linux. Most engineers who use EDA tools are into linux so having to run a few things on Windows is a pain. The 'A' in EDA stands for automation and Windows is not the OS for that. I installed a standalone WIN10, then enabled the TPM and installed WIN11. Seems pretty solid but I had to guard against MSFT repeatedly trying to lead me into servitude.

I don't think it is just big companies. I worked for startups and small companies; when there are a number of managers/VP's involved there is trouble. Bad ideas persist because managers/leaders do not throw stones at each other. As an engineer I tend to just do what makes sense then justify it afterwards; I have trouble with managers who are just administrators with no relevant technical background.