I find David's line, 'I'm proud to be your son' a bit strange, unless he means you're a good leader and I'm proud of that. David could not be proud of Kirk's paternal skills since he channelled his paternal skills on a large chunk of metal called Enterprise.
By STV Kirk forgot he had parents, a brother, nephew and a son with his 'people like us don't have family' line and 'I lost a brother once, but I got him back'.
Kirk would fill up a therapist's pension pot with his issues.
I think that was David's way of saying he was wrong about his judgment of Kirk and who he thought he was.
About those lines in ST V, the family one is more along the lines of "men like us don't have families of our own", meaning they are not suited for marriage.
And the brother one... if he had said "I lost
my brother" instead of "I lost
a brother", I might agree with you. Saying 'my' definitely means he only considered Spock his brother and totally forgets about Sam, while saying 'a' implies he had more than one brother... in this case, one biological one and one by deep friendship bond, this one being Spock.
How do you figure? I'm interested in what examples from TOS inform your opinion
"SPACE SEED", for example. He goes to engineering himself to get the ship under control.
Same with "THE NAKED TIME" after Scotty gets the door opened so he can get Riley out of there and stop the ship from burning into the atmosphere.
Though to be fair, Kirk did not know the internal workings of the refit
Enterprise nearly as well as he did during his command in TOS. (TMP shows this explicitly at least twice, when he was asking for directions and when Decker countermanded his phaser order.) Now, he may very well have brushed up on her inner workings since TMP, but Kirk not running down to engineering himself to help solve the crisis keeps with one of the themes of the movie: Kirk feeling old and worn out.