It might have been good if "Family" had included a subplot of seeing him directly go from not just My career plans are my own business to my place is on the Enterprise though there was some subtext of that in TBoBW including that he decided to yes throw away the book and/but not let Picard go, that he had to save him.
I've always felt
Family had the perfect opportunity to touch on this, when in the very 1st scene, Riker & Worf are conversing about Worf being bothered that his parents are coming aboard unannounced, & Riker sort of takes their perspective on it.
There was a good opportunity, even if just for one scene, to have Riker talk about how he might even be jealous about not having any family at Earth to come pay him a similar visit, his mother being long dead, & his father, while being somewhat less estranged, is still distant, and that some crew, like himself, come all the way back to their homeworld, & never reunite or see anyone, because the ship & crew ARE their only real family.
Something even as simple as that one exchange might've given some tangible context to how Riker feels about the people there, & why he's still surprisingly there, after being offered another option. Having an episode called
Family, about some of the crew's relatives, without at least bringing up Riker's deal, seems a loss, & it could've been a much more potent thorn in Worf's side to hear himself whining about family
wanting to see him, to someone who might actually want that but doesn't have it, & is choosing to make it for himself right where he is, at the possible cost of his future ambitions.