One puzzling disappointment was why didn't the ninth and tenth films bring back the idea of romance between Picard and Crusher?
I get that Generations (aside from being too soon after "Attached") and FC were already busy/packed and with Insurrection Stewart wanted a romance-of-the-week but the movie probably would have been better without it and instead with a second renewed attraction among the crew. And then there *really* should have at least been a renewal by Nemesis especially with Riker and Troi getting married, Picard feeling particularly lonely and the movie being the last one with the cast. I guess maybe the last movie was instead implicitly saying that Picard missed his chance but that feels too disappointing and underwhelming.
To be fair, there are a few deleted scenes in Nemesis hinting at a renewed attraction, or flirting at least, between them but of course they were excised from the movie. The original ending (with Picard talking to Crusher over comm link as she settles into her new role at Starfleet Medical) has the dancing doctor inviting him to dinner and, after he declines, promising Jean Luc that she'll save her last dance for him

It was a shame those scenes were deleted, but also that they came out of nowhere in the first place. It would indeed have been more fun to have seen them set it up in Insurrection as they did Riker/Troi.