I guess it is a risk/reward thing. Sometimes you just want to shoot-the-moon. If you REALLY want to do it and the people affected agree, why not? It’s your life.
That being said, my father told me of the time he flew an SNJ through Hangar 1 at Moffett field. It was not long after WW-II and there were lots of young pilots with nothing to do and lots of avgas to do it with. Needless to say, many questionable things happened back then. (He looped the Golden Gate in an F8F too.) I liked best the end of his story which went, “As soon as I entered the hangar I realized this was a REALLY BAD idea. Unfortunately I was committed.”
I had a similar kind of decision to make. After flying around the world following Amelia Earhart’s route I had an airplane with which to fly Lindbergh’s route and set the speed record from NY to Paris. I would just have to fly over the N Atlantic in February to take advantage of a positive phase of the N Atlantic oscillation and get the winds that would let me shatter the old record. I had to consider the threats, i.e., engine failure and icing, consider the risk of possibly dying in the cold water of the Atlantic, and then balance that with the reward – a plaque on my wall that said I had the speed record.
I didn’t go.