I've experienced multiple instances where (so I heard; I don't use Windows) a Windows Update completely broke a game on Windows for everyone, but Wine/Proton kept running it just fine. So we're already there in some sense.

Windows 14 will just be a linux distro with wine acting as backwards compatibility.

It feels like it won't be long before Microsoft starts helping with that (by making Windows less stable, not improving Wine).

Wine actually does run some ancient Windows games better than Windows 11 itself.