I actually really enjoyed the Charizard nostalgia episode of the anime. It was very well written, and Ash seemed very fleshed out as a character, going on about his past experiences with some level of knowledge. He seemed so self-aware, especially when he was talking about how helped Charizard unfreeze in the Orange Islands.

They should do more episodes just like it. Ash often seems like a robot or empty vessel the way they characterise him, but this episode made him seem much more human.

I hope we get to see more touching moments in the anime.