I think software is going to the direction of emulation anyway.

At this point you have platforms like Electron, which run in a browser environment. Java software which runs inside JVM. Now there's even linux sub-system inside windows, etc.

I think there is a way to do it the other way around. MS put effort in creating something similar to WINE and make a special "Windows POSIX", which let's say for the next decade is released along with the classic Windows ( Same as NT before ). Where they try to emulate / rewrite the software piece by piece until the stability is reached to switch.

I don't see this as an impossible idea to me. Actually if they did something like this I will be so happy to switch back.