About Worf in the KDF: I think it does make sense – a fuss was made in one of the pre-Destiny TNG novels that Worf will never be allowed to command a Federation starship, owing to that mission he failed in DS9 to save his wife. Thus I could see him joining the KDF to gain a command of his own once he felt he had achieved all he could/wanted to in Starfleet.
It's not like there's actually something written down somewhere forbidding Worf from becoming a captain. What he did in "Change of Heart" is a serious blot on his record, to be sure, but other Starfleet captains have comparable or worse things in their histories. Jim Kirk was court-martialed twice, and the second time he was actually guilty, but his actions subsequent to the crime made up for it and let him keep -- or actually resume -- his command. Captain Picard lost a starship under questionable circumstances and went through a harrowing court-martial, but still managed to earn the right to command another starship, the flagship of the fleet, in fact; and then he lost
that ship and still got trusted with a third. Kathryn Janeway did all sorts of legally and ethically questionable things in the Delta Quadrant but still got bumped up to admiral. Chakotay's a former member of a criminal organization, but he's captain of
Voyager now.
So given Worf's mostly exemplary service as a Federation ambassador and Starfleet first officer in the years since, I really don't think it would be impossible for him to earn a command if that was what he wanted. Especially since the Borg invasion devastated Starfleet and they can't afford to turn away any good candidates.
Although the Klingon fleet is far more militaristic than Starfleet, there’s nothing to say what sort of missions he was flying before the whole Hobus/Romulus/Nero/Space Octopus thing happened. Surely not every Klingon mission is about killing and smashing?
That's beside the point. The point is, it shouldn't be assumed that just because he's genetically Klingon, he's somehow destined to end up in service to the Klingon state, as though his life experience and Starfleet loyalties meant nothing. Race isn't identity.
About the TNG crew breaking up by the time of Countdown: Particularly in the case of Geordi I think this is a good thing. Who wants to stay in the same job for 25 years? How long can the poor guy stare at that big warp engine and stay sane?
If you're in a job you love and excel at, why would you ever leave it? Why should ambition override contentment? My job is writing novels and stories, and I'd be happy to stay in that job for the rest of my life, assuming my financial needs were met.
Besides, Picard has been a starship captain for most of the past 48 years. He's found his niche and has rejected offers to be promoted out of it because it doesn't make sense to put arbitrary career advancement over doing the job you love best and do best.
Although I will say that the idea of Geordi leaving Starfleet to design starships makes more sense than the idea of him leaving engineering to become a Starfleet captain. There's too much tendency to assume that every other job in Starfleet is just a stepping-stone to a captaincy, which doesn't make any sense, since there are always going to be far fewer captaincies than there are officers.
In Picard’s case, I can’t see him wanting to raise his child on a spaceship. Him becoming ambassador to Vulcan ties in neatly with not only the TNG finale, but that Picard/Sarek mindmeld episode.
But why would the Federation need an ambassador to one of its own founding worlds? Does the US have an ambassador to Pennsylvania?