Just skimming through here. Some interesting ideas. I really love the idea of Data taking over as captain after Generations. I mean, that's like a couple years between Generations and First Contact that we don't know what the character was up to. There's also space to explore after Insurrection, and you could play around with the aftermath of the Dominion War if you went that route.
While I would be tempted to have Geordi and Troi on the Sutherland with Data, I like the idea of Hobson more. Hobson is already established, he can be a respectful foil, and still someone that challenges Data, but also is challenged by Data. There's more there when it comes to interpersonal conflict and drama with Hobson as the first officer.
If you did want to have other TNG characters in your series, I would look at the supporting characters. I mean, where are the "Lower Decks" characters at? Or Taitt or Barnaby from "Descent"? TNG had a lot of interesting supporting characters that it would be nice to see get more spotlight.
For stories, why not look at revisiting
, Sela, and Lore? Thus far, we don't know what happened with Lore and Sela, and there's still a lot we don't know about
as well.