Luffa luck is too much. Always doing stupid things and then winning in the end is boring
you can think punching the CD would have made Luffy more careful but no : Jumping Dragon Kaido, fighting in the middle of the fest etc etc.
at least when Kid is doing things against powerful guys he pays it : one arm against Shanks, jail + Killer being SMILED etc
luffy has way too many free pass
Luffy is the freak who shocks other freaks. That is his M.O.
Why would a TRUE conqueror tuck his tail in between his legs. The CD are trash and he'd do the same thing again.
Luffy came prepared for his round 2 properly learning a whole new chain of haki, Kidd and Killer hoped for the best, and you call it an unfair plot free pass? lol.
Kaido wanted to make Luffy his slave, that isn't just luck, that is supported by in universe character motivations of Kaido to create an army to fight the WG. Kidd didn't lose anything directly from being jailed.
Orochi didn't get an opportunity to interact with Luffy's crew in the same way and all of them would have had unshakable faith in Luffy.