Lol, Luffy refuses to break, that's why he gets stronger. You have tons and tons of examples of people who refuse to take the chances he takes, and they're generally older, so I'm not sure about being surprised. Especially in the shonen mold where the main character getting stronger is usually less explicable.
At the same time, he'll take an L when it comes. He doesn't delude himself or get into denial; look at the execution in Logue Town.
We all know Luffy is the "Chosen one" in One Piece world.
However, while "Chosen one" is typical for manga, I do admit that Luffy irritates me the most.
In my opinion, the chosen one character should have some unique attributes.
They might have a unique characteristic, different thought process, or inherit a special power. This makes him special in the manga world.
However, we still perceive or feel that those chosen ones will get same penalty like other characters if they did the same mistake.
This is not the case for Luffy.
Luffy got defeated by Kaido just similar to Oden and Kid. However, the consequences they got are massively different.
Kid was put in jail forever like Ace. Oden just got killed after his first defeat.
At the same time, Luffy has luxurious to get defeated by Kaido for 4 times, and to get rewards from those losses instead of bad consequences.
He found perfect teacher, perfect training camp, and unlock multiple power ups.
Personality wise, Luffy is just a stubborn child like Kid and Ace. However, everyone loves him at first sight. Naruto, Deku, etc. still needs to prove over time that they are worthy. This is again not the case for Luffy.
To conclude, One Piece is a world where characters are treated with double standard. For me, this makes Luffy a boring character and ruins the world building and tension as we all know nothing can touch Luffy's invisible plot protection.
Note: I am sure Luffy fans will drag Zoro into the conversation.
Luffy is unique in that he is macho, assertive, and competitive without those being his defining features. He's below-average sized, nose picking babyface in a world of buff hairy giants, and he'll spark anyone without thinking twice. From Vivi to Aokiji, anyone can get it. In fact the fight with Aokiji is a great example of character because the latter is like, "...did you really think you could win?" Luffy clearly understood the gap in power, but he just knows that if he ever gets into a fight, he's gotta better fight with the full confidence of winning no matter what. And yes his bloodline is part of the reason he got off easy... but that's not at all something he'd think about or care about.
No, he's not the same as Kid or Oden. Kid's ambition is self centered and ultimately his aim can change based on what suits him. Fight Kaido again? Maybe... but he'll settle for tag teaming Big Mom because he's better off. Oden fights for others and like Luffy will prostrate himself for the benefit of others, but this n1gga had Kaido dead to rights and said "don't come back!"
Luffy on the other hand was no match when he challenged Kaido, and so he wasn't a threat worthy of death. That worked in his favor because each and every one of the people who can't be certain they'd beat Kaido pipes down. Look at the gorosei right now. Look at Doflamingo shitting himself at the idea. Luffy has bigger balls plain and simple, and he never asks for special treatment.
Ah but let's go back to Kid if I'm gonna address your comment in order. Didn't this man meet Rayleigh at the same time? Wasn't he in the jail with Hyo before Luffy? Did he get turned down, or did he actually fail to make a good impression on them?
Because personality wise Luffy always makes a good first impression. Actually no. Ace, Hancock, Whitebeard, Shanks, Zoro, Kaido, Kid, Katakuri... those are just the conquerors, for the sake of making my point.
I didn't read the other responses yet but rest assured I can keep going about this without dragging Zoro, my favorite character lol