Following up on #1:
So, after Googling random things from the Mono debug log, I found this bug report which mentions the Mono 3.10.0 release notes says that libgdiplus.dylib is basically broken currently. And if I understand correctly, this affects most winforms-based programs running under Mono on a Mac.
I eventually found a fixed version of Mono, which acutally works! I was able to open an .hws file, enable a modifier option, and save out the modified save file.

Considering this currently would require an unreleased version of Mono, do you want to just leave this issue open until Mono has a new official release?
Following up on #1:
So, after Googling random things from the Mono debug log, I found this bug report which mentions the Mono 3.10.0 release notes says that libgdiplus.dylib is basically broken currently. And if I understand correctly, this affects most winforms-based programs running under Mono on a Mac.
I eventually found a fixed version of Mono, which acutally works! I was able to open an .hws file, enable a modifier option, and save out the modified save file.
Considering this currently would require an unreleased version of Mono, do you want to just leave this issue open until Mono has a new official release?