In my mind, this is an important bug report. Often when you deal with users, the problem is between the keyboard and chair: "The calculations are all wrong!" "Yes, that's because you uploaded an excel spreadsheet with all the wrong numbers..."
But sometimes it isn't the users fault. Sometimes programs crash because you made a coding error. So you fix your code and the users become happy.
To me, this story is the latter. Guy didn't do drugs, isn't a suffering a mental disorder, have a gambling problem, alcoholic and still becomes homeless! Then I think the problem can not be blamed on a user error, but is a system problem. Perhaps this user didn't behave exactly as the system programmers expected, but there still needs to be enough error handling builtin so you don't get homeless from the errors he made.
Supposedly he tried his best and he seems like a smart person. I think a very large part of the population would have taken even worse decisions in the same situation.
But sometimes it isn't the users fault. Sometimes programs crash because you made a coding error. So you fix your code and the users become happy.
To me, this story is the latter. Guy didn't do drugs, isn't a suffering a mental disorder, have a gambling problem, alcoholic and still becomes homeless! Then I think the problem can not be blamed on a user error, but is a system problem. Perhaps this user didn't behave exactly as the system programmers expected, but there still needs to be enough error handling builtin so you don't get homeless from the errors he made.