An interesting write-up
@Lord Agragax of Lunaxoatl . While everything you wrote is correct, I believe you are wrong (and I will try to explain my rationale)

. I used the term "wrong" but not in reference to the merits your analysis, but rather what you have chosen to analyze. A story is an emotional journey and we experience that emotion vicariously through our focal character, which is usually the protagonist of the story. Let me give you an example...
Let's say we have a story about a war torn country that is facing an invading force that is thought to be far superior to them and is hell bent on eradicating its citizens. Enter our focal character, a mother of three small children. Her husband has perished in the war and things look bleak. Our story encompasses her decision to risk it all and cross her country so that she might flee with her remaining family into a neutral country where they will be safe. She is advised against this course of action because it is an extremely dangerous journey (especially with small children in tow) and she will never make it. Against the advice of those she trusts, she sets out to reach the neutral country with her children. Throughout the journey we experience the story through her eyes. When she is in danger we experience the tension alongside of her. We see her flashbacks to better times, and we smile with her. When there are close calls throughout the journey and narrow escapes we hold our breath. When she is relieved, we are relieved. When she is happy, we are happy. When she is sad, we are sad. When she is terrified, we experience that emotion as well. Okay, let's skip forward to two possible conclusions to our little experimental story...
- The mother makes it across the border with one of her three children. She was separated from the other two and they are believed to have perished. Leaving her child in safe hands, she prepares to go back across the border the border to hopelessly search for the other two. Just then, her husband, who was believed to have been lost in the war, shows up with her remaining two children, safe and sound. There is a tear filled reunion and our little story family is safe. He explains how he had survived and how he had been trying to find them all this time. Over the radio, we hear that her country has fallen to the invaders; it is a complete loss, the people of the land have been eradicated. She listens to the news as she cradles and comforts her family.
- In the second scenario, we find ourselves with the mother who is within a kilometer of the border. She frantically searches for the two children she was separated from. She eventually comes across their broken little bodies. She is devastated at their loss and feels guilty that her decision to make the journey has gotten them killed. Very reluctantly she must leave them behind and carry her remaining child across the border. We see her running towards the border as gunshots can be heard. Mere meters away the mother is hit by a bullet and she falls to the ground. She has taken the non-fatal wound to the arm but her focus immediately shifts to the child who has been fatally struck and dies in her arms. Her world is shattered and she lies there holding her child's still warm body. Darkness takes her. When the story resumes, we find that she has been carried across the border to safety and is in a hospital. As she regains consciousness, her thoughts focused purely on the loss of her family. Her heart is broken and she weeps. In the background, a television is running and the news anchor explains that her country has somehow miraculously repelled the invaders and saved its citizens. The news means nothing to her, all she can think about is her lost family.
So in which story have we experienced greater loss? In ending #1 we have an entire country that is in complete ruins. It's people have been murdered and all has been lost. But on a personal level, the family is safe and the focal character (the mother) has achieved not only her goal but has been reunited with a husband she thought she lost. In ending #2, the entire country is saved. It's people, it's culture and it's sovereignty have been maintained. There is celebration in the streets. However, our focal character (who we experience the story through) has lost everything.
Ending #1 In the big picture we have a complete loss, but a touching personal victory
Ending #2 In the big picture we have a victory, but personal tragedy
So my point in all this is one that you made yourself...
This is what really matters emotionally in a story. Everything else is just a backdrop used to experience the story through the viewpoint of our key characters. If hypothetically you have a beloved character die in an X-wing that is more sad and dark than losing an entire capital ship filled with thousands of "nobodies". That is how we are wired as human beings, we care most for those in our inner circle.
Armed with that, let's re-examine our movies...
Empire Strikes Back - Our focal character, Luke, loses everything. He abandons his training with Yoda thinking he can win the day. He learns painfully that he was absolutely wrong. Vader bests him in combat and takes his hand. He then finds out that the worst guy in the galaxy is his father (remember at this point [chronologically by release date] the emperor is nothing but an unknown background character). Han has captured and Luke throws himself off the ledge (choosing what he must assume would be death over joining his father). That is emotional stuff. There is a huge amount of personal loss. The music and the ending of the movie all reinforce this. It is the most somber point in the entire movie franchise.
Revenge of the Sith - There is a great amount of personal loss here as well, but the execution is lacking. The primary character, Anakin, loses everything. He becomes a traitor. He loses his wife. I believes he has lost his children. The Jedi order is gone. He is bound in servitude to Sidious. This is all pretty emotional stuff as well, but we have a few problems (some of which are due to poor execution, while others are the unavoidable byproduct of this being a prequel). The first problem is that the silliness of Padme dying of "sadness" removes much of the emotional impact of her death. Next, Anakin is a very disliked character in the prequels (not because he turns evil, but because of his portrayal and whiny nature) so it is harder to feel for him. In addition, Anakin becomes the villain and ultimately we are seeing the villain pay for his crimes (while Luke is the hero and is willing to sacrifice himself rather than join his father in evil). Lastly, some of the impact is lost because we already know how the story ends This is something that afflicts any prequel story. The film's close is intermixed with hope in the form of Luke and Leia. I don't want to shit on ROTS because I think it the best of the prequels and I do really enjoy it. However, it does not have the emotional impact of ESB.
The Last Jedi - Here there is virtually no personal loss (other than for real life Star Wars fans

). Yes Luke fades away, but Rey and Leia seem to understand and accept it pretty easily. Plus, Luke was a bum in this movie to begin with. Overall the mood in the Falcon is pretty jovial and the music in the background reinforces this. Sure the resistance has lost a great deal, but things aren't even that bleak. They have Rey who should be able to stomp the whole first order single-handily. The only villain worth fearing is dead (unless they retcon it) and the remaining leaders are either largely incompetent (Kylo) or an absolute buffoon (Hux). Sure the first order has massive Star Destroyers, but now you can just fly kamikazee droid piloted smaller craft into them at hyperspace velocities. Nothing in the end of this movie even comes close to recreating ROTS, let alone ESB.
Rogue One - The issue with this movie has always come down to the characters. I know you love them (and I am not trying to convince you otherwise), but to the vast majority of people, they were flat, boring and forgettable. If you can't connect with them, then you don't emotionally experience the story. Yes they all die, but aside from K2, nobody (or very few) people give a crap. We also have the same prequel issues as we had with episode III, we know how the tale concludes. In the end, what is the ending of Rogue One remembered for?... Vader finally being portrayed as people imagined him to be, as he slaughters the rebels (very cool scene by the way). However, none of this has the emotional impact of episode V. The personal loss is negated because most people don't care for the characters. Also, as you said, they still win this engagement... which leads to a greater victory in the future.
While a largely disagree with your conclusion, I must say it was a good read. You are correct in many ways, but I view the movies through a different lens. Overall, it made for the most interesting exploration I have had on this thread. Your write up did allow me to see the topic through a different viewpoint and while I ultimately feel a different way, it was a worthwhile engagement.