I wonder if they could have mitigated that by leaning more heavily on the ability to have multiple personalities running on top of the kernel. So for instance, you could run a program from 1996 on the "Windows 95" subsystem and get better compatibility, but Teams could run on the "Windows 11" subsystem that treats CON as just another file name. Of course, there might be a problem if programs at different compatibility levels interact with the same files, but there's actually precedent for dealing with that kind of thing quasi-transparently, or perhaps I should say QUASI-~1.
