Ten years ago I read a "news of the wierd" story about a young homeless man in silicon valley. He earned something like $90K a year working as a junior programmer or some such occupation. He slept under a bridge, but had a bank account, mailbox, cell phone, laptop and gym subscription. He worked out and showered at the gym every morning before work. He socked away lots of money and spent a lot of his free time surfing the internet at a coffee shop or other hang out. The reason the story got picked up is that his parents or someone in his family was trying to get him committed for psychiatric treatment. Its more bold and daring than most people but that behavior in and of itself doesn't really sound crazy to me.

A long time friend of mine wrote an article for the New York Times about her boyfriend's decision to become homeless.