Yes, the app constantly harped on the drone needing calibration. When I hooked the drone to the laptop and launched DJI Assistant, it would briefly show the calibration instructions and then come up with a warning message that I needed to reboot the aircraft. Once I followed the above mentioned procedure, I was able to successfully calibrate the vision sensors. I just now hooked the drone up to my Win 10 laptop and once again was able to successfully proceed with no error message about rebooting the drone. I'm going to say that the guy giving you advice, knew not of what he spoke. It looks like I could calibrate the sensors as many times as I wished.
I know nothing of how Macs work, but I'm going to say that my problem was caused by file permission errors on Windows. I imagine the Mac also has something similar.