It's pretty counter to Microsoft's incredible investment in backwards compatibility. Or Linus' "don't break user land" philosophy.
I'd think if we had a spectrum of backwards compatibility, with the most being on the right it might look something like this:
OpenBSD ---> macOS/iOS ---> Linux ---> Microsoft
I think in the OpenBSD case, due to limited developer resources, and a cultural bias towards simplicity, this is the tradeoff they decided to make. Even at the cost of more users.