Debug Issues in Mac OS X
Nevermind my last question, seems I have figured it out.
Solution was to change my stm32f4discovery.cfg file to use stlink-v2-1.cfg instead of stlink-v2.cfg.
Figured this out after finding my PID in the system report window within the About This Mac preference, and seeing that it did not match with the current PID configuration.
Thanks for your time and all the help Laurent!