Maybe I'm being a bit black-and-white on this, but while the meta and the philosophy is interesting to talk about, no one is mentioning the morality. Stealing is wrong. You're taking someone else's work and not compensating them for it. I think it's sad that we're all so worried about the law when, in reality, you shouldn't pirate music for the same reason you don't steal a candy bar from the grocery store or snag 5 dollars out of your coworker's wallet or hack into Dropbox to get extra storage for free. It's wrong.
It's very impressive that he's able to earn so much money and support his family via Craigslist, but I can't help but think about how useful (or not useful, really) his job is for the overall economy. Basically, he's another middleman - buying goods for a low price and selling them higher. Without him in the picture, buyers could have purchased their items for less and saved money. I just don't see how this job adds a service to society.