As the title implies, i find this aspect of Ash's character a bit jarring.
Why is it that the show made Ash so inexperienced, naive and immature compared to every other trainer he meets? He obviously loves Pokemon, as apparent by all the merchandise that was in his room, so why doesn't he know a lot about them? What was stopping him from learning everything he needed to know about Pokemon before starting his journey?
What's more, every trainer that could be considered at the same level as him (just starting on their journey) always seems to know something that makes them superior to Ash in some way, why is that? The only reason that i can fathom why Gary knows more than Ash is because his grandfather is Prof. Oak, who is also a good friend of Ash's family, why didn't he learn from Oak prior to his journey? And why is Ritchie smarter than Ash, why is every trainer smarter than Ash in some way?
I could more or less understand why Misty and Brock are smarter, they are Gym leaders after all, but why make Ash so inexperienced? And while we're on the subject, what did Ash do to lose Charmeleon's respect?