While that’s certainly true, I’m pretty sure it’s intentional. I think whether it works for you or not comes down to if you ultimately think Rian was being smart or pretentious.

Luke is there to challenge Rey, Rose is there to challenge Finn, Holdo is there to challenge Poe - they essentially are antagonists for our trio of protagonists from the previous movie. I very much assume you’re supposed to dislike Holdo, because Poe is the audience surrogate for that plotline and he certainly dislikes Holdo at first. Ditto for Luke - many people talk about being shocked and disappointed that Luke is so unlike his old self, but that’s because Rey is your audience surrogate there, and she’s also confused and angry that he’s not the Luke Skywalker she’s heard of in the myths. Perhaps to a lesser extent with Rose because the audience doesn’t necessarily agree with Finn’s plan to escape and save Rey, but later on when he just wants to get the Canto Bight plot line over and done with, whereas she wants to save the fathiers, I think it applies.

I can’t help but feel adding in some positive interactions at the start of each relationship just to then pull the rug out would only add to the feeling that the movie is hyper-obsessed with never doing what the audience expects. I do agree that the way it is in the movie might lead to some people not “forgiving” the antagonists when they redeem themselves later in the film, even though our protagonists do.