I also think it's more of a challenge to make movies in today's atmosphere, given that one side or the other of the most vocal segment of the audience is going to be all over you for how your choices are viewed through a social justice lens. Either you lack representation or are pandering to diversity, and so on.

I would say Empire had more courage of its convictions in that regard, where tLJ tried to be upbeat and fun and gratifying. If Empire was like tLJ, Leia would have come striding in to use the Force to rescue Luke and humiliate Vader. Lando would have been more of a villain, like Del Toro's character, rather than a guy whose compromises caught up with him and left him between a rock and a hard place, who paid for his equivocating in lost trust and failure of his effort to make amends (the critical delay while Chewie chokes him with Leia's approval, while stupid on their parts and probably allowing Boba Fett just enough time to escape, is the blowback of Lando's own past betrayals)

While I agree with the substance of this point, I have come to actively dislike the citations of Campbell & the Hero's Journey, by critics and defenders alike of the various movies and plot elements. "But they followed the blueprint" or "they have deviated from the rules" are arguments that say nothing about the quality of the work.

Those rules and forms and whatnot are post hoc explanations for how storytellers think, not a checklist for telling a story. The fact that tLJ did what others did before it, does not absolve the film or its makers for failure to entertain, anymore than "I deployed my troops precisely according to the tactical manual" excuses a defeat in battle.

Luke for Poe...maaaybe. It's an interesting notion, because I think a lot of people also get distracted by the immediately obvious parallel of Rey and Ep5-Luke. But Leia & Holdo are not really a good comparison to Obi-Wan & Yoda, given their direct involvement in the action, and sharing of blame and failure detracting from their capacity to teach lessons to the lead characters.
Good stuff, but Holdo was not in a remote location where Poe came to her for lessons, she is holding a position of command and trust where lives depend on what she does. Yoda is free to teach Luke or not, and Luke is there of his own free will. Holdo's moral duty, as Poe's superior, includes guidance and teaching, as much as his duties to her include obedience. Her solutions do not solve problems any more than his would have, and people are dying while she asserts her superiority. And as the commanders on the scene, ultimately, the responsibility for Poe's failures falls on Leia and Holdo. Either Poe has the right to use his initiative independent of Leia's authority, or she is ultimately to blame for following his bad plan to bomb the dreadnought. I also don't see much difference in trading a wing of small craft for a dreadnought, or trading a capital warship for a dreadnought, not to mention her kamikaze run destroyed the world-building. It's a Game of Thrones-worthy bit of spectacle where the filmmakers clearly have not thought about the ramifications for the rest of the story, just throwing it in there because it looked cool. If warships can perform adequately with a single operator at the controls, why did Leia need all those people on the bridge who died because of a fighter attack motivated by a personal grievance and whom her sudden Force abilities failed to save. It feels again, like trying to have their cake and eat it too, by head faking her death, and then a surprise save because she finally uses the Force. You could have done the same thing with the bridge crew floating in a bubble that Leia could struggle and sweat to hold together, and fly them back, and then collapse, and no one would think to challenge that (I don't agree with all the nonsense that her survival and Force use violates space rules or established limits of the Force when much of Yoda's dialogue in Empire should have disabused fans of such notions). Her Yondo routine also undermines the theme of failure, saying that because SHE'S special, she has a get out of jail free card.

The optics of the film don't help, when you have a white authority figure, wearing a gown that suggests wealth and privilege, instead of a uniform indicating service and self-abnegation, condescending to a Latino for his emotional and passionate brashness.

But the distribution of that failure is uneven. Leia and Holdo are not presented as failures by the narrative. Even Rey's dangerous flirtation with the Dark Side comes across as more of an "OK Boomer" to Luke's crotchety observations.
Are we looking at the same Mark Hamil?
But again, when the man is wearing the garb of a warrior who risks his life on the battlefield, and the women are wearing impractical gowns, and when the actual content of their advice is no better, but the narrative treats them like the voice of reason... that's muddling the message. In Empire, Leia dressed like the other fighters. General Reikan had a much better operation going on Hoth, and largely succeeded, in contrast to the panicked and hurried evacuation we see in tLJ, that doesn't really do anything.

Leia & Holdo are kind of like Tyrion, where we are supposed to assume he's always right and Daenerys is always wrong in their moral discussions, even though she is making good points if you think about it and has a rather more successful military track record. And people had the same complaints. People PROUDLY rejected chunks of Season 8, because it was about men telling a woman how to behave, even though they had credentials, like familiarity with the people said woman was trying to impress. The narrative of GoT is that the hero(ine) eventually snapped after everything went wrong for her, and circumstances beyond their control rendered her male advisers' counsel useless. The narrative of tLJ is that the hero kept bucking older and wiser heads, who actually knew what they were doing all along, while he kept bringing disaster on their heads, until he was confronted with it and learned his lesson. But neither story is what we saw with our own eyes. The events that played out did not match what the authors were trying to show. Even Poe's side mission that ends up with DJ betraying the fleet to the First Order, happens because of the leaders' failure of oversight, in assuming that a guy who does not sit down and shut up when they tell him to, is going to do it THIS time, and NOT go behind their backs.

I would say, trying too hard to be Empire, rather than successfully capturing the spirit of Empire. I'd say Attack of the Clones does that much better, however inferior a film, and more subtly, by having the failure seemingly redeemed by a triumphant rescue, except it isn't at all. Because the viewers know what's coming, because they use the same music for the mustering of the clone army that they did for the deployment of the battle droids on Naboo in the previous film, we can understand as well, that these clones are bad news. They have not rescued the Jedi, they have simply co-opted them into their leader's design. tLJ ends with Rey being awesome and a deus ex machina who retroactively makes all their plans not suck. It's more like "The Dragon Reborn" where even though Rand is off in his own story for most of the work, his arrival at the end saves everyone. Except the point of tDR was that everyone's piece of the fight matters, and that everyone has to try to do their best, regardless of what they want, if they feel up to it, or how much they've suffered before. With some tweaks, tLJ is very close to telling that story, but they tried to stick to the Campbellian/Original Trilogy blueprint that said their story was supposed to be about learning and growing from failure. Instead, we get the impression that Rey is the Dragon Reborn, which doesn't sit well with a lot of the fans, and undermines her own actions. Her arc is fine for someone who's trying to figure out how to be her best self and act with the hand she's been dealt. Not so much for the indispensable savior figure.

And they blew it with Rose's final line, which out of context is good, but unfortunately, we got in the context of that movie and the Star Wars saga in general. The big thing for the hero of each of the trilogies was to learn his limits, because he's wield a scary amount of power, fraught with real danger. Anakin does not accept those limits, but Luke learns to. You don't see Rey's equivalent of a failure at the tree, reinforced by ignoring her mentors and proceeding to plunge in over her head and get her ass handed to her and need to be rescued by the people she presumed to be saving. Instead, she dabbles with listening to Ren, and doesn't pay any price, rather, gets to eliminate a significant enemy and a number of his most dangerous henchmen. The narrative makes her leaving Luke more like his failure then hers, whereas in Empire, it was also presented as Luke's failure, but he was the protegee instead of the mentor. But pertaining most to this movie is the line of Yoda's, when Luke asks if he should just let Han & Leia suffer rather than run off to save them, "If you value what they fight for, yes!" Anakin failed that same metric with regard to Padme. He valued her companionship more than what she fought for, and destroyed the Republic she spent her life fighting for, to get the power to "save" her. He didn't respect her choice.

And that's what Rose does when she diverts Finn's ship. She doesn't fix anything, doesn't make it any better, and the only reason they don't die uselessly, being stranded on foot, with one of them unconscious in front of the enemy lines, was the out-of-nowhere appearance of Luke (who was no one and nothing to either of them) enabling Finn to drag her to safety. It's stuff like that and Leia's Force thing that make it feel like some characters have something more than plot armor, they have writer favoritism, that lets them survive mistakes or avoid having people notice their faults and assign blame or face any need to confront their failures themselves. Finn was flying at the weapon to save what he loved. Luke flew off to Bespin to save what he loved. Ren backstabbed Snoke to save what he loved. Poe attempted a coup to save what he loved. Anakin turned to the Dark Side and Luke gave into his anger on the second Death Star, in an impulse to save what they loved. That statement, without some substantive action to back it up, is pointless in the context of the bigger story. Rogue One, arguably the most selflessly heroic mission in the whole saga, was made up of people who were nasty bastards arguably looking to strike a blow at something they hated. They didn't have any single thing they loved in mind. The mission was not about saving the Rebellion or a specific planet or people, since nothing was explicitly threatened yet. It was just a bunch of guys who hated what the Empire had driven them to do, and said 'fuck it, let's take this chance to strike a serious blow' rather than play along with the leaders' conserving strategy. Rogue One bought victory with their lives. The resistance fleet, following the orders of Leia & Holdo and in the spirit of Rose, saved the lives of the elite, front & center characters, at the cost of everything else.

And everything about Canto Bite.