I'd argue that First Contact's critique of Federation ideals is uniquely pointed because it aims that critique specifically at Picard, who is constantly shown t

I'd argue that First Contact's critique of Federation ideals is uniquely pointed because it aims that critique specifically at Picard, who is constantly shown to be the conscience of the Federation, the one who insists on those ideals even when others argue that the exigencies of the situation demand compromise. His character mirrors Worf's in that way - just as Worf values Klingon ideals far more highly than the other Klingons we see, Picard does the same with the ideals of the Federation. It might be part of why they get along so well, but it's also worth considering that Worf's idealism is founded on detachment - he's able to indulge in it because he's in a position where he almost never has to deal with the messy realities that make idealism so difficult to sustain. One wonders whether the same might be true of Picard. Unfortunately, we don't get a chance in B&B-era Trek to see how he reacts to the test of the Dominion war, but his behavior in First Contact is nonetheless telling. If even "the conscience of the Federation" so signally fails to live up to the ideal - if it's only the desperate intervention of someone from a time universally regarded in Picard's own as a cesspool of cruelty and horror that saves him from his own mad, vengeful hatred - does that tell us something about the merit of the ideal? If even the person who most exceeds all others in following its guidance can so signally fail, are we wrong to question its value as a guide for those less uniquely exceptional? I can't disagree that Discovery and Picard are very different from what's gone before. But, then, the TNG-era works were very different from TOS, too. Where we differ, I think, is that I don't see anything wrong with that - indeed, I don't see how it could be any other way. The works are made in the context of, and in dialogue with, their times - as you yourself note with regard to TNG and DS9. These are very different times from those in which the earlier shows were made, and it would be much more of a surprise to see new Trek shows try to ignore that difference than to see them embrace it. "Infinite diversity in infinite combinations." It's a worthy ideal, and an apropos one to see expressed in the same series of TV shows and movies whose own originator codified it.