ao486_MiSTer VS winevdm

How about a 486 instead? :)

https://github.com/MiSTer-devel/ao486_MiSTer

Have you checked all the details in https://github.com/MiSTer-devel/ao486_MiSTer ?

You mention "Pentium MMX CPU" a few times in your post, but fail to mention any FPGA solution that can emulate a machine of that class. MiSTer can't do that, the best it can do is a 486 (not just missing MMX, doesn't even have an FPU).

It has already happened: https://github.com/MiSTer-devel/ao486_MiSTer

The last processor generation it worked on is the 486, but on a Pentium or newer it always fails with a “Debugging is not allowed” message.

I guessed the reason for that correctly - prefetch queue. Mentions of CUP386 in the comments also brought back more memories of the cracking scene in the late 80s/early 90s. There's some very interesting discussion on SMC vs CPU behaviour here --- in the context of an open-source 486-level SoC core:

https://github.com/MiSTer-devel/ao486_MiSTer/issues/33

Not exactly what you were asking, but winevdm [0] does use code from Wine to run 16-bit Windows applications on 64-bit Windows installs that don't support it natively (via ntvdm).

[0] - https://github.com/otya128/winevdm

https://github.com/otya128/winevdm run 16 bit apps on 64 windows

This, along with Windows's own compatibility mode tweaks, should run almost any game that has ever been released on Windows.

WineVDM: https://github.com/otya128/winevdm/releases

It could work with the help with otvdm: https://github.com/otya128/winevdm

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winevdm enables you to keep old Windows programs on life support by running 16-bit Windows (1.x, 2.x, 3.0, 3.1, etc.) on a 64-bit Windows system. Ojakobe explains, "Had a special case of a user who clung to their Windows 7 PC because their work was reliant on a 16-bit program from 1997 (and even on 7 it didn't run properly). Used the program above to make it run reliably on 10."

After that you should now be able to install software. One final sticking point is that some older programs are wrapped up in 16-bit installers, however these can be installed by running the installer with something like otvdm.

Try WineVDM because NTvdm never got a port to 64-bit since the CPU mode it relied on for fast 16-bit code execution gets disabled when a x86 processor is switched into long mode. WineVDM is likely translating 16-bit instruction calls to 32-bit and then passing that off to Windows