Wine on Windows is technically interesting, even if others might argue that it's pointless. At the very least, these are also good tests of how much compatibility the layers provide.

There's also WineVDM that actually solves a "need" to run 16bit Windows programs on 64bit Windows. I've considered using it for retro programming without leaving a modern OS, although DosBox may be a more reliable option. Now, if Win32s can get to work on top of WineVDM, that would be funny.

This something I'm currently working on - for both Msys2 and Cygwin.

https://gitlab.winehq.org/jhol/wine/-/commits/msys2-hacks-7/

There's a few low level issues to solve, but also theres bunch of patches around that never made it upstream that just need some love to get them up to standard.

At this point Msys2 installs, we can run bash and install software using pacman (- with workabouts for varies janky problems).