There's a huge disconnect here between criticizing Riker's career trajectory and the actual values of TNG... which was that career choices were a personal matter. Troi, Worf, Wesley a lot of characters had non-optimal career choices in the process of finding themselves and the show didn't look down on them for it.
I mean part of the point BOBW was making was that RIker's cautious experience is still valuable over his younger ambitious Shelby type personality where he just wanted to make captain. We have to assume Starfleet was wise enough to recognize that and continue to offer him commands because they want that mindset in command
I'll let Picard boil it down
It's all right there. Being the 1st officer is no substitute for being the leader. Riker is the substitute commander of the Enterprise. By sitting back, aspiring only to take over someone else's command, it literally shows a lack of vision, & ultimately undermines your would-be authority. A leader leads. They don't sit around waiting for some dream job, least of all when someone else has it. The big wigs don't want a dreamer. They want a leader
I mean part of the point BOBW was making was that RIker's cautious experience is still valuable over his younger ambitious Shelby type personality where he just wanted to make captain. We have to assume Starfleet was wise enough to recognize that and continue to offer him commands because they want that mindset in command