I recently posted an ad to sell one of my high end basses on CL and recieved tons of response. Mostly lowballers, crazy trade offers, etc. So yesterday, I get an email from a guy that proposes a fair trade right off the bat and it is gear that I actually want/can use.
Anyways, the coolest part is that once I get on the phone with him to figure out the details, it turns out he is a pretty famous guy (in a hugely famous band) and he will soon be playing in front of 20,000 people in my town. I mention my kids love his music, and bam! 4 back stage passes for the concert!

Turns out he is a great and down to earth guy.
In any case, the weirdest deal I did was when I sold a Sadowsky a couple of years ago on CL. I was asked to meet the buyer at a gas station late at night in the middle of nowhere. He shows up... in a big white Hummer and 4 HUGE guys get out and try out the bass. He slaps almost $2000 in hundred dollar bills in my hand and off he goes with the Sadowsky. I thought for sure I was going to take a bullet or get thumped out!