Ask IBM how well that idea worked. I think it's fair to say that OS/2 had better Windows compatibility (for it's era) than Wine offers (in this era). The problem was that Microsoft introduced breaking changes with the introduction of Windows 95. While old Windows applications would continue to run under OS/2, IBM felt that it would take too much effort to introduce a compatability layer for Windows 95. If I recall co…
The latest multi-platform packaging systems like Nix or Flatpak have largely solved the binary compatibility problem but providing some guarantees of library versions. This approach makes more sense in modern contexts with cheap storage and fast bandwidth.