@dc42 I had double and triple checked the wiring and thought everything to be ok even moved the head around manually and tapped the bed with no issues. I went ahead and secured the wiring harness a little better and wouldn't you know it, was able to complete auto calibration multiple times.
Wiggled the wiring while tapping the bottom and can see that it does in fact seem to be a crimp issue. Just happened to be in the right spot every time I checked it that and the fact that it failed on the exact spot led me to believe it might be something else. Going to re-crimp everything and see what happens. Will update when that is complete.
Thanks!!