"Also when you take it to the extreme, If something managed to hold 100 times it's far more likely to hold the 101st time compared to something that managed to hold 3 times not breaking the 4th time."

Interesting thought experiment. I'm curious what leads you to make that conclusion? From my understanding, a support is strong if it holds 2 or 3 times but anything more than that and it becomes weaker and weaker (especially assuming smaller bounces from that support every time).