Then it went out again two more times, and it happened when the outside temperature was below zero.Yesterday and today there were four broken pipes. 

They'll get broken. 

A falling walnut has never broken a cars rear window in recorded history. 

Also, things can get broken during the course of a normal tenancy.

I fix broken things but not cosmetic things that they were aware when they took the place.

I just replace a broken water heater on a SFR that has been in service for about 7 months.

You have to do that in order to achieve what he's achieved and it comes with sacrifices:  2 broken marriages, enemies, lawsuits, all that crap. 

They have to have broken the "rules". 

It could have broken.

I understand there is a reason for policies and rules however, if someone's income falls $25 short of 3x rent, excluding a reasonable car loan [I personally say pay cash however, operative word being ... personally] no significant monthly outgoings and obviously, e no prior at-fault broken, unsatisfied leases, I would say go for it.