I have a personal story of the "buy a plane, crash a plane" category, or in my case, "(I) sell a plane, (they) crash a plane"...and they crashed it without ever technically flying it.
Many years ago, I owned a warbug, a 1942 Taylorcraft L2M. It was a beautiful aircraft, with full logs (including military logs), painted with stars and bars, and only about 2000 hours airframe / 400 hours engine. After flying it for a few years, I got tired of only going 85 knots wide open, so I put it up for sale. I negotiated a deal with the new owners, and as part of the deal, we agreed that I would deliver the plane to their flying group.
I was given directions on getting to their second "secret" hangar, because they wanted to introduce the plane in a ceremony the following weekend at their main hangar. Both hangars were at the same field, but at different ends. When I arrived at their field, they ushered the plane into their second hangar. I told them that because it was a very old airplane, I'd like to go over the whole plane with them and explain its "ins and outs". They refused, saying they knew more about the plane than I did. I told them I wasn't selling the plane without going over it for my own piece of mind, and then they reluctantly agreed, but I could tell they were only appeasing me and not really listening.
One of the things I tried to show them was my method for hand-propping when I was by myself. I would turn the fuel on, prime the engine, shut the fuel off, then hand prop. With the fuel off, the plane would only sputter-start for about 4 seconds, giving you just enough time to jump into the cabin and turn the fuel on while being ready on the brakes. As I showed the new owners, they got annoyed and one of them said, "We will NEVER start this plane by ourselves. This is a waste of time."
After going over the rest of the plane, they flew me home, as we had agreed. I found out that during their ceremony the following weekend, they crashed the plane. Seems that two guys were getting ready to bring the plane to the main hangar for the ceremony. With one, a pilot, in the plane, the other hand propping it, and it started. The propping guy then jumped in his car and told the pilot, "see you at the other hangar" and drove off. The pilot gave the cold engine too much gas and stalled the engine. Soooooo.....he got out, hand propped it with no one in the plane (and the fuel ON with full or nearly full throttle) and the plane started, took off with no one in it, and crashed.