Giving a customer a break.
Today, I ran into a short of cash customer who left me very uncomfortable. He has repeated his order 14 times in the last month. Today, he was short of cash and asked for a "hail mary" until Saturday. I decided to take a risk and told him, ok, I'll let it go this time, but please don't make a habit of this. Only two days ago he told me that he was going through personal bankruptcy proceedings. When I arrived at his door, he was quite upset. Apparently, my comment about making a habit of this, had really embarrassed him.
What is the correct way of handling this?