I imagined Picard as an ambassador. I thought after the Enterprise, he’d do some admiraling but find that he could be more useful as an ambassador. Perpetual captaining was Kirk’s thing...he liked being on the scene, keeping active; the admiralty was too macro for him.
I don’t think Picard would have followed Kirk’s advice too long past GEN. He’d become an admiral at some point but find that he liked being on the scene in a diplomatic capacity, influencing relationships first-hand. Admirals win wars, ambassadors prevent them. I think Picard would have been invaluable in that way — setting up relationships for prosperity to flourish.
Riker I imagined captaining the Enterprise after Picard and then becoming an admiral as in “All Good Things...” Then Titan happened, so maybe Titan, then admiralty.
Data I imagined slowly becoming more emotionally sophisticated, eventually being as “human” as anyone, long after all we know have died. His nature is an immortal one, so I’m okay with him having relationships after these in his formative years. Though, it would be cool if at some point many years down the line, some mission brings him back to these old friends. Ultimately, he’d have an immortal family and people of his own.
Crusher heads into command in her later years, figuring modern medicine is a younger person’s game. She’s captain of her own ship and saving lives planet to planet. She and Picard marry and have twins together who take turns visiting her on her ship or him in different places whenever they’re not all together at the vineyard on Earth, or wherever else they’re do family-time together. Everyone is constantly in motion, but it works. The nurturing and the love are there.
...that’s one version. Maybe in another she goes back to Starfleet Medical so she can live on Earth with Picard and the kids on the vineyard. A second home on Luna where she grew up like some have a second home by the shore to go away to? ...It would be interesting to know more about what that looks like. Is it terraformed; does she have family there? Is it alien from what we’re used to?
Geordi installs himself Emperor of the Pakleds? Okay, I’ve gotta go. Maybe later...