The reseller needs the money he makes too. This guy was clearly in a bad situation when he started and being a "wheeler dealer parasite" provided for his family that needed the money.

How is this worse than someone who needs the item getting it for free?

Respectfully, I would encourage you to find someone personally to give your item away to. Craigslist is not a charity, it's a marketplace for people to buy/sell goods. Giving away an item on Craigslist is like throwing bread to ducks at a duck pond. If you indiscriminately throw bread up in the air at a duck pond, would you blame a squirrel for coming by and snatching a bagel every once in a while?

Nobody forced you to give him the stuff. As long as he's not lying about what he does - and we have nothing to indicate that he is - the seller is free to make that decision for themselves.