lol
I get what Brian is trying to do. He thinks that by giving his kid options (even at utterly retarded moments like allowing him to dictate training), he isn't driving the kid towards the type of cobra kai lameness that pervades himself. He very often refers to the options he gives the kid in response to any pushing about whether he's doing the right thing.
Still, that aside, he is still doing exactly what his parents did which was cart him around looking for low hanging fruit to boost the ego of the boy so that he has an impossibly high opinion of himself to get rebutted in adulthood (and become the same chip on the shoulder that Brian has).