https://bugs.winehq.org/show_bug.cgi?id=46236
--- Comment #14 from Ken Thomases ken@codeweavers.com --- That suggests to me that this is hitting a limitation of the 64-bit support on macOS. There's a technical barrier to properly supporting 64-bit Windows apps on macOS. Wine has a partial workaround, but there are still cases that won't work.[1]
It seems like this program, when compiled by VS2017, is hitting one of those cases. That may be because of different code being emitted by the compiler or because of different code in one or more statically linked libraries.
[1] https://stackoverflow.com/questions/53244454/how-did-wine64-manage-to-handle...