I've been sitting on this thought for a bit, and I think the reason that post-XY Ash was so off, despite the fact the writers were trying to make him closer to Indigo League, was because he wasn't a looser anymore.
Original series Ash? He's constantly outmatched by Gary, constantly being compared to him, and how much he's fallen behind him. He was dumb, and not in the Shonen Protagonist way, but just in the way a kid is going to be dumb. It's natural, not forced. Ash isn't dumb because he's dumb, like post-XY, he's dumb because he just doesn't know a lot yet. His Pokemon are all scrappy. He's got Pikachu, that won't stay in the ball like any other reasonable Pokemon. He has Caterpie, a bug-type that anybody else would have ignored. He has poor Charmander, Bulbasaur and Squirtle who were all abandoned by their original trainers. The cool thing is that he never gives up. Yes, he's behind. Yes, he's not as talented as other trainers, but he doesn't give up.
I think that's why Sun & Moon and Journeys Ash just comes off as so weird in his personality. It doesn't make sense for his character. It also makes it harder for the audience to connect to him. The original audience was mostly kids. Kids understand that 'the cool kid' will tease them. They understand that they will make mistakes and be berated about them. Kids also love the idea of having freedom to explore and do what they want to do. It's the same reason Charlie Brown appeals to so many people, he's trying so hard, but things, more often than not, don't work out for him. That's why people cheer so hard when the looser does win, because, in a way, they're winning too.
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