Thanks, I will give that a try! I found d3d9 and msvcp but apparently missed msvcr. So naturally I figured the hacked dlls weren't compatible with WINE, or something like that, just kind of back burnered it. I have just been using 1024x768, it's not too awful.
WINE on Windows is kind of a thing. It's obviously a low priority for the devs because... why, right? But it's the only way to run 16-bit software on 64-bit Windows. This is also pretty much how Microsoft implemented 16-bit support on true 32-bit versions of Windows, although of course they didn't use the WINE code, but their own compatibility layer.