Since getting back in the hobby in 2005, I've probably sold over 60 games. The double-haggle has happened to me a handful of times. The following were the most interesting:
1) T2 - Buyer agreed to my asking price over the phone but wanted to negotiate when he arrvied. Two reasons he gave while begging me to lower my price: 1) He drove here in the rain. 2) He wanted to tell his wife he got a deal.
2) T3 - After a thorough inspection, buyer said he wanted it, and he handed me an envelope. I helped him and his friend get the game ready to load, and then as they were moving it to the vehicle, I started counting the money. It was $400 short of my asking price. When I brought it to his attention, he said, "I thought we agreed to that price over email." I quickly looked over our emails, and I said, "Nope, we never talked about price." He ended up leaving because he said he didn't have any more money with him. However, he called 5 minutes later saying his buddy had $150, and he asked if that would be enough to buy the game. It wasn't, so he ended up going to an ATM for the full amount.
3) Not a pinball, but a '65 Dodge Coronet I had listed on Craigslist...Buyer agreed to price on phone, but he was driving 3 hours with a car trailer. He wanted to make sure he wasn't wasting his time if I ended up selling it while he was on his way. He assured me he would pay my asking price. I told him I wouldn't be able to sell to anyone else because I would be at work when he arrived, and my wife would have to meet him on her lunch hour. I called my wife before her lunch hour ended to make sure everything went well, but she said the guy left without buying because he offered her less, and she said no. She was on her way back to work when he called her back and offered the full amount. Now he had to wait about 3 hours for my wife to get off work.