I wounder it the problem you were having with the bike tires was air leaks on the sidewall where higher pressures would push out for a tighter fit. In high school I took a consumer auto class and we had to make a hole in a tire and then plug it and that is much easier to do with a well inflated tire than a lower inflation tire.
I was told that the higher pressures provide greater resistance while rolling. I think in shop conditions it's easier to puncture a well inflated tire because those conditions are closer to off road conditions than on road conditions. Think of it in terms of the size of area being punctured and the lenght of time the object used for puncturing is in contact with that area. I would bet that in the class you identified the point of puncture, set the puncturing tool against that point and applied consistent pressure until you pierced the tire. I would also bet that most of the time you chose a puncture point in the canyon of the tread, rather than on the ridge where it would be a lot thicker. Also, do you think that you have gotten the same results if you just took a quick, random jab at the tire?