A shot like that comes across more as a boy with his toys than a guy with varied interests.
Honestly, it comes across as bragging more than.. hire me.. I have varied interests. Or.."I have expensive hobbies and you're going to help finance them."
I'm not a fan of justice scales or law books behind them either. Too cliched.
I find good solid portraits that shows a compassionate, approachable and confident person will do the best.
All that aside.. it's a nice shot.
Yeah, he was concerned about looking like that, but he did want to be in front of his plane and/or bike and he does some work in those areas so with those guidelines this is what I came up with. Plus he's obviously kind of a unique character and he wants to set himself a little apart from the competition so I do think a shot like this in a legal magazine accomplishes that. But I agree with your points in general.
To the other guy, I'm not sure if he was ever in the AF; I think the plane was painted that way for a movie.