I've sold a number of audio/music gadgetry on the old craigslist. Usually I can find a buyer willing to meet at a neutral zone, and willing to pay my asking price, or at least close to it.
But my worst CList experience was when I made a vehicle trade with a local fellow. He needed a gas-saving commuter, and I wanted a pickup truck to haul my ATV around. Thought I'd had a done deal until he hits me with a bombshell. There was a second owner on the title that just HAPPENED to be a used car dealer, with an outstanding balance on the truck. I was lucky to get away with only paying a part of the balance, but it was still a shock. Then the lovely conversation with the dealership sales manager that went something to the effect of "Your buyer forfeited this vehicle to me, and I can't transfer ownership until you've signed off too. I've already reported my vehicle sold, and I'm not in the habit of driving around in an unregistered truck. As for securing the remaining balance your customer has on this truck, that is a conversation you'll want to have with him."
I felt like a champ for how I handled the situation, and the dealer dude signed off on the papers. Not that he was happy about it either.