Perhaps the lack of empathy is because he's masking it. I would appear much worse off than that guy, I don't have a car, I don't drive and I live in a tiny apartment with my wife. This guy is 'homeless' and lives better than I do!
I've stayed in youth hostels for $80 a week that were secure and offered me a free breakfast in the morning. So yea I think he could manage without the chains, some people just don't want to lose thier lifestyle.
I do hope he gets back on his feet and I think this is a great way for him to get his name out there, if so this is a great reason to it!