You can dress it up anyway you like, folks have "personalities" that tend towards different kinds of behaviour, Tom's seems to be one of breaking the rules if he doesn't think they apply to him at his skill level. So after he gets a couple of thousand hours in an airplane and has done some approaches to "hard IMC mins" is he going to now think his skill is good enough that those mins don't apply to him? If I was a betting man, I would bet he would, not someone I want flying my property, family, etc around.
I have a bit of a vested and thus bias interest in this, because the area he was dicking around in is where my two nephews live, one is only 11 and has a physical handicap, last thing he needs is to be hit by some dumbass joyriding.