Some of my thoughts.

Fixletdebugger On Osx Using Winebottler

I have the Windows Fixlet Debugger working on OS X bundled into a .app using WineBottler.

Download here: https://dl.dropboxusercontent.com/u/640753/FixletDebugger_9.2.9.36_OSX_WINE_SIGNED.zip

Note: This will be running under the WINE context, which thinks it is Windows XP. This will not work with OS X only relevance, and it may not work with all Windows based relevance either. I have not tested this enough to know what works and what doesn’t, but I still think this could be useful.

You can recreate what I did by downloading WineBottler and use the following settings:

All files in folder, Set DirectDraw to GDI

This may be an option for many Windows Only utilities on OS X. The Session Relevance Tester comes to mind.