I’d always try wine (x86) first. I remember a friend and me wanted to play Dungeon Keeper 1 a couple of years ago and after fiddling around with Windows 7 for ages we finally tried it on Linux using wine and it worked out of the box and even simulated IPX. Now, about a decade later, I’m using wine for pretty much everything, not only games.

And if wine doesn’t work for you, try pcem. Might take some more time to set up, especially because you’re aiming for a win16 app, but it’s also closer to the original hardware (because other than wine it’s an actual physical device emulator).

Did you know that there is a debugger in Jetbrains CLion (and I think VS as well) that allows you to step through your CMake scripts? As ridiculous as this may seem, actually it is really useful.