Naitch
Reads history books
Jack Roush has 2, Ted Christopher and Mike Stefanik from the modifieds. I agree it seems like a lot, though I think statistically its because like you said they fly a lot.
They also fly distances that most people would drive. Dale Jr’s deal happened when he was preparing to go to Bristol and the Hendrick crash happened flying to Martinsville. Bristol and Martinsville are 3 and 2 hours by car from Charlotte respectively. I would feel safer in a car than a private plane.
In most sports, athletes fly via a chartered commercial flight, which is WAY safer than a small private plane. I saw a study once that said that commercial flights were 200x safer than those taken on a small private plane.