he is a ding dong, but he's not naive about how the world works, and I think there are many who woobie him because he hasn't let cynicism and his own harsh upbringing destroy his childlike curiosity and optimism
I agree with you that Luffy isn't naive about how shitty the world can be. I also feel like Luffy doesn't always pick up on context clues either, because he has a very specific way of looking at things
plus, his idea of "take what I want" is genuinely stuff like food and maybe treasure, with the caveat that he's not colossally dicking anyone over or robbing them of their freedom
lmao! so Luffy. Luffy is very intelligent about people, strategy, fighting. It's true, he's not exactly naive, or dumb, but stuff goes over his head if he's not interested in it.