Two good ones below, once as a seller and once as a buyer:
First, a tale of woe as a buyer.
On the Chicago DSM Mailing List circa 2003 or so there was a 99 GSX with a bad motor being sold for $750. Complete car, good title, dude just had to have it gone. I am home from college on spring break, so I call Dude, he has bad english (eastern European) but tells me he will be home at 4 PM and gives me his address. Its about a 2-3 hour drive for me from Wisconsin, so I gas up my truck, grab my floor jack, pancake compressor, basic tools, run to my friend's house to scoop up him and his dad's trailer, and head off to Chicago. Get dicked by some tolls, but get there no problem. Find the house, not in too bad of a neighborhood. Knock on the door, dude's dad answers, has no idea where dude is, calls him, tells me he will be there in 15 minutes, and I should head around to the alley.
Pull around to the alley there is a 20 yard rollback half full of dirt and wet concrete blocking the whole garage. While we are waiting, my friend and I pop the door on the garage and look. Its a gorgeous car, slightly disassembled, but all there, 5 speed, nice mods, resale red, etc. We unhook the trailer and hook my 250k mile 95 F150 to the back of the rollback with a chain, trying to drag it. No dice of course. Try jacking it up to roll it, no dice of course. Dude shows up, and I ask him why he told me to show up when there was a dumpster blocking the garage. He apparently doesn't live at home, and didn't know the dumpster was there. He ended up giving me $50 for gas, told me the dumpster would be moved in a few days and he would call me. Never called me, I ended up driving home with the license plate folded down around my trailer hitch and blowing all the tolls. At least we got some Burger King out of the deal.
Second, a tale of humor as a seller:
I was a senior in high school and knew very little. For $250, I purchased a sweet 88 Cougar XR7 that I had plans to pull the motor from and put in in my RX-7. The Cougar was all there, but ran rough (bad coolant temp sensor maybe? tons of black smoke) and the paint was bad. The interior stank too. It had 3 good wheels and a donut spare. Everything you would expect for $250.
As with most well laid plans, the Cougar and RX-7 mashup never saw the light of day. I realized this a year later when I was off to college and short on cash that I should sell this turd. An ad is placed on the old Excite Classifieds and a couple of White Trashies from Wisconsin Dells call me up. I tell them the car is at my parents' house, they are welcome to call my mom and arrange a time to go look at it, but no rush as it isnt leaving till spring time as its at the bottom of a hill and snowed in. I get a call from my mom an hour later, wondering why some idiots are driving down to look at a $500 Cougar in the middle of a snow storm. They make it down, leave $250 deposit, and my dad tells them they can come get the car once the snow is gone and the ground is good.
So the weekend they are coming to pick up the car, by blind chance, I am home. They tell me they will be coming around noon on Saturday. We get the car pulled up the hill, it takes a jump and runs but won't restart. Battery is cashed. Position the car on top of the driveway and wait.
4 PM comes. Mr White Trash and his girl finally show up. In an S10 with a Uhaul trailer. This Cougar weighs more than an S10. They told us that the S10 had the fuel pump die on the way down.
Picture this. The car is at the top of a medium hill, facing down a driveway. An S10 is backed up the driveway with a trailer. This S10 does not have a good parking brake, so a floor jack is used to keep it from rolling. The plan, concocted by the White Trashies, is to roll the Cougar down the hill onto the trailer. Now a Cougar, with no power steering or brakes, is not known for its stopping prowess, nor were these brakes good to begin with.
The Cougar is rolled down the hill, hits the trailer, and takes flight. It ends up with the front of the car touching the tailgate of the truck. The truck has rolled forward onto the floor jack popping the tire of the truck. Mr White Trashy is freaking out, he is trapped in the car because it came down into the wheelwells of the trailer and guess what- no power for the power windows.
In an act of heroism or sheer stupidity, Mr White Trashy KICKS THE WINDOW OUT OF THE CAR! He crawls out, surveys the damage, and starts cussing. My dad, being a better man than I, calmly gets a floor jack, a bunch of 4x4s, and 2x12s, and gets the Cougar back on the trailer. We even happen to have a spare wheel for the S10, so we get 50 bones for that, and get Mr White Trashy fixed up and headed home. I hope he liked his Cougar.