It is a thing, yes. A friend of mine was discussing how he has to think about the events to go to because his key man insurance on his family office requires hi

It is a thing, yes. A friend of mine was discussing how he has to think about the events to go to because his key man insurance on his family office requires him to use his own pilot, so he's contently inventing dumb reasons not to go to things vs admitting his cheap and doesn't want to spend the money. Two things I find amusing about this... rich people being cheap is always funny, and, as you mentioned, insurance companies preferring a private pilot when flying private it less safe. Apple requires this for Tim Cook too, and I always thought it was amusing.