I think "Tommy" is perhaps indicative of "how he is being raised." He's being treated, still, as the baby, as the overly doted-upon only child. My concern is that he's not being taught many responsibilities. With a wealthy father, he may not have to work to earn any of his perqs. I don't know, and perhaps it's not my place to presume, but from this brief essay, at least, I get the impression that Tommy is spoiled rotten.
I do not think it is tongue in cheek. I believe Ben does have a loving relationship with Tommy, but perhaps not a parent-as-authority-deserving-of-respect-and-obedience relationship.
I've been reading Ben Stein and his 'Tommy' for many years and thought the way idolized his son was going to lead to trouble.
Well, let's hope he does well and keeps on the straight and narrow.