I've got plenty of crazy Craig's List transaction stories. I think the absolute weirdest was selling my Step Dad's Honda Oddyssey. He passed away in 2013, and my Mom said seeing his van in the driveway made her sad. So, I took it home, cleaned it up a bit, took some pictures, and posted it on Craig's.
About five minutes after I listed it, I got a call from a man with a very strange accent. "You sell van. I come now, money. You text address."
I texted my address to the number, and about ten minutes later, he called again. "I'm outside now. You come out."
I came outside to my parking lot, and saw the man looking over the Oddyssey. What was very odd was the fact that he was alone, and no other cars were nearby. So, he had been dropped off with cash. I said hello. He was clearly familiar with the weak points of the Honda, the air conditioning and the transmission. He got in the van, started the engine, turned on the AC, and held his hand over the vent until it blew cold. He then opened the hood, pulled out the transmission dipstick, and proceeded to smell and taste the fluid.
"AC and transmission OK. We have deal!" He pulled out a neat stack of $100 bills, with the final bill wrapped into an origami band around the rest of the bills. He then glanced at the gas gauge, hovering right above empty. "Wait a minute... fifty bucks gas!" and held out his hand. I reached into my pocket and gave him the $40 that was in my wallet. He then handed me his stack of cash.
I said "great, let's do the paperwork", holding out his half of the title and a pen. "I no have time!" He handed me a piece of paper with a name and address scrawled on it, grabbed his portion of the title, and sped off in the van. The entire transaction took less than five minutes.
I walked into the house, and my wife, who had been watching from the doorway, said "What the hell just happened?" "I don't know... I have money and my half of the title... we can make this work." I called my Mom and told her to call the insurance company and take the Oddyssey off of the policy. "I'll do it tomorrow." "No, Mom, do it now. A strange man just fell from the sky, handed me origami money, and drove off in the van. Do it now!"
I filled in the Release of Liability portion of the title with the information the man handed me, and immediately took it to AAA to submit it and get it out of the family name. Everything happend so quickly, that the next morning, I realized that I had left my sunglasses in the van. I called the number the man had called me from, but it had been shut off. The address, in Fountain Valley, was on my way to work, so I tried to find it. The address didn't exist.