I do wish him well, and I hope he finds the happiness he's seeking. The thing is, he thinks having nothing will make him happy, and that the money was making him miserable, but happiness/joy comes from inside, not from external circumstances. I wonder if he'll be happy just because he's homeless?
My thoughts are that it's just as easy to be happy when you're rich as it is when you're poor. I've not been rich... yet... but I have been very poor and on the brink of homelessness, and I've been solidly middle class for years, and everything in between those two points, and I can say for sure that money doesn't make you happy, but neither does being broke. Joy is not dependent on your circumstances.