I've bought some and sold them later, but all of those were picked up with the idea that I wasn't planning on keeping them for long. With those, I have no regrets. For the most part, I think long & hard about handguns I'm buying for myself, so I don't tend to EVER get rid of them later.
But a situation presented itself to me and I still have some regrets...
The deal was, I knew a guy who was moving out a number of his guns. The one in particular was a S&W Model 19, Texas Ranger commemorative. This was a 1974 (I think?) build, pinned & recessed of course. He bought it many years back from some other guy. It was in the commemorative box and also included the matching knife with matching serial number.
The revolver had never been fired, but it wasn't in absolute 100% condition. The grips had some surface scratches and one little chip and there was a definite turn ring on the cylinder. Nothing at all wrong with it, mind you, but I'm just pointing out that for a commemorative, it was lacking in "perfection" as commemoratives are supposed to be. His price was $650, but after getting no bites on it, he drastically lowered that price to me.
I had another buddy who had been looking for his first .357 Magnum. He loved my 6-inch 686 and was considering a 686 or a GP-100. When I told him that I could snag this one for $400 if he wanted it, it wasn't a tough sell.
I told him that he would be paying at or under market value for a beautiful K-frame .357 Magnum, but that if he shot it, it wouldn't really be a "collectible" commemorative any more. That was my idea-- spend $400 on a nice S&W and shoot it, regardless of it's "collectibility."
He liked that idea also, so I agreed to pick it up for him. I made no money on this deal. I had actually bought a few guns from the one friend, and this is one I sold to another buddy.
So when he came to pick it up... with the cool wod box with the etched Ranger emblem carved in to the wood... the pretty blued factory finish... the cool Texas Ranger emblem on the sideplate of the revolver... the matching knife... he decided that he didn't want to shoot it.
And now it just sits at his house, where I can visit it often but I can't shoot it. He bought a 6-inch stainless GP-100 about two weeks later and shoots it regularly.
Recently, he did take it out and put some rounds through it, so I have the green light to shoot it also when we next get together. But if he'd do it, I'd give him the four hundo back and take that revolver and put it in MY safe. It would be a regular shooter.
Now it makes me really want to find a Model 19. Doesn't have to be a Texas Ranger model, but something from the early to mid-70s sure would be nice. And unfired for $400 would be even nicer.