The thing I don't like about Last Out Post is how awesome Riker comes off.
He realizes it's a game, what the rules are and how to win. Smarts and balls.
As the years went by, where did his smarts and balls go?
Is it because the first few handful of episodes were in a mirror universe where this was an entirely different man named Bill Riker?
(Check the script.)
Aside from the obvious "plot needing him on Enterprise" why didn't he accept a Captaincy, since the show repeatedly stressed he gave up any semblance of any sort of normal life (lovers, family, friends) for his career?
He was offered a dinky little ship in the Best of Both Worlds 1. In the second episode, that ship was destroyed by the Borg. At the end of The Best of Both Worlds, Will was told that he could have the pick of any ship in the fleet, and his reply was something like "Why is everyone so concerned about my future, when I'm still dealing with my present."
Riker was also offered a ship in the one where his dad shagged Pulaski. Kyle went on to call his boy a loser for turning down his own ship to stay in Picard's shadow because that's how real men parent.