Two spring to mind, I misunderstood a guy over a deal involving a cheap Spanish non ejector I wanted to get rid of, he talked about a deal with an English double he had, it turned out (too late sadly) he meant he wanted a straight swap, it was a Field coil spring sidelock similar to the one B.Graham on this site has. It was in good shape but I thought he meant the Spanish gun and my cash for it, so turned him down. He sold the gun on for peanuts and gave me 50 for the Spanish boxlock. Doh !
The other was a grubby but beautiful 20 bore Harper single barrel hammergun. It was at a local auction with a starting price of 60 (iirc) I decided I'd go up to 150 but there was a last minute bidding frenzy . Commission aside, I'll bet the seller was happy that day.