I'm thinking that the Dominion War situation with Picard's Enterprise might've been like with Pike's Enterprise during the Klingon War, where Starfleet sent a few of their best and brightest far away from the conflict just in case everything went really badly for the Federation. That could be another reason why Starfleet ordered Picard to stay away from the battle in First Contact, other than having doubts about Picard's reliability regarding the Borg.
Yeah. I enjoy trying to figure out where story arcs are going, but that feels like empty calories after a while. By the 80% point of the arc, any remaining mystery should be "How are the protagonists going to solve the problem?", rather than "What are the characters' secrets, and what exactly is the threat?"