Retro68 VS winevdm

If you can live with cross-compiling from a modern PC (or Mac) you can use https://github.com/autc04/Retro68 which uses a recent version of GCC.

Alternatively, you could install Executor 2000 (sort of a Wine-like clean-room reimplementation of Macintosh System 6 for running on other OSes) and get into classic MacOS programming using the GCC-based Retro68 C++-17 toolchain.

Strongly recommend checking out Retro68 and cross compiling from a newer machine: https://github.com/autc04/Retro68

There are some really good Retro68 code examples out there as well. I started compiling a list here, including a couple of my own: https://henlin.net/2021/12/21/Cool-Retro68-projects/

As a few other folks have said, the inside Macintosh books are extremely valuable references for Mac-specific code. I keep pdfs of them open the whole time I’m working on my Macintosh projects.

if you want to go period-appropriate, you can run Macintosh Programmer's Workshop or CodeWarrior natively

I use retro68 on linux, which is a modern GCC toolchain, so it's just like developing any other C/C++ (well, without some nice debugging tools, and with the added complexity of the mac OS resource stuff)

https://github.com/autc04/Retro68/

personally, I think retro68 (port of modern GCC for vintage macs) is way nicer to use than any period-correct compilers or IDEs.

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