I agree with Ian - this looks like the same crash. For my money, I suspect that Mono is looking for a dependency of some kind, not finding it, and then not handling the exception elegantly (read: crashing). From the very diligent re-installations you've done, CP, I don't think the solution will be in Mono, but in the OS.
So if you were going to persist with the Mac, the suggested approach would be to image the current OS to an external hard drive, install a later MacOS version as a fresh install (i.e. don't just upgrade), then install Control:Mac and restore user data from the external drive. Of course while this will be excellent in terms of diagnosing the software, it does require an OS change and all the drama that brings. So reverting to Windows looks like a sensible step in the meantime!