Snooper, IMHO, there are two factors here. Firstly, DM was emersed in aviation. IMO, instead of going to the playground when he was a kid, he was hanging out in an old hangar at Pearson with his Gramps and friends. Secondly, DM was an only child and only grandchild of 2 aviators- nothing would make them happier than to have one of their own break a record in aviation. IMHO, the childhood of DM was less than optimum for social development with his peers. Perhaps offering "the good life" to people, the things that only money could buy, was the way he finally learned to make friends.
But over in MS's life, he was the son of a middle class, run of the mill family. IMHO, MS is an open book. Typical non motivated type in school (do we know where he went and if he even graduated?), no expectations of college or university, some questionable friends, a pile of gal pals that just wanted to hang with him, a few "risky activities" and the best highs that his money could buy...however much money he had at the time. MOO