re: How do people let themselves get into such dire straits financially?

I think most people don't expect the worst, then they dont do anything about it til they have no options. He's probably been holding out for that job that will pay him the same money he was making. Instead of just taking anything. Plus much like our politicians no one wants to say no you can't have that or you have to wait til we have enough money for that. See how TOPS, Medicare, and Social Security are working out.