I feel him losing in Kanto worked against all the dumb luck wins he got in that era (even if they kinda failed to make his loss feel connected to that rather than just being unfairly screwed by a series of events of everyone being apathetic about it).
Honestly Meowth in boots was pretty cool, it just didn't deserve to be introduced only to defeat Ash
Really I feel like the wasted potential with it was around Team Rocket's Meowth (I've already discussed how most of his rivalries end up one sided and undercooked besides Pikachu in my analysis thread).
Considering how popular his character still was during DP, I don't see why him winning the Shinou League would've been the right time for him to be replaced. That said, him winning the Shinou League would've only been realistic to me if Takuto hadn't competed.
I Guess you're right. Tobias only serves his purpose as a Roadblock to Ash's Final goal which makes me annoyed to this no extent by having no time for him to explain his backstory, Does he have a backstory if he's a roadblock?
It’s not about popularity. It’s about his character arc and the narrative coming to a close. As others have mentioned, Sinnoh very much felt like the culmination of Ash’s journey up until that point. He had a smaller arc within each saga too.
It was clearly a factor to some extent, otherwise they could've simply replaced him back then, especially since they would've also had the perfect excuse of Black/White being the first post-Kanto games that were purposely designed to be a "fresh start", ergo the greatest opportunity to change the status quo in the anime aswell.
Alola only feels like “a waste” because it’s not the same as your typical league or regional tournament when it’s NEW.
I also feel like Alola kinda works as a character realization for Ash, where he has fully wound down from the egotistical character he started off as and has learned to appreciate the world around him and that the league is only one blip of the grand scheme of it all.
This too, and this point gets amplified even further by the fact that, IMO, the Alola gang is arguably Ash's closest companions. No hate to Brock, Misty, Dawn, May and the rest, but SM is the first series that actually feels like Ash has a very close relation and emotional tie with the setting he's adventuring through since he doesnt travel constantly in Alola like he did in Kanto - Kalos. He's not going to one place as fast as he quickly leaves another place like in the other regions
Exactly. XY Ash may grow in the seriousness department where he's focused on getting stronger and winning the league title, but he suffers in the department of actually enjoying Kalos. Even in Hoenn and especially Sinnoh when Ash matured and was super focused on battles, he still took the time to enjoy the adventure through those regions and wasn't stuck thinking about one thing through and through.
I like how it works in the sense of being a total antithesis of what Kanto was (at least originally). The original series conveyed Kanto as horrifically serious business, leaving Ash a very insecure and frustrated character as a result of how harsh and judgemental peers were around him (which we know in Shudo's original plans was because the whole Pokemon trainer occupation was toxic and based around 'git gud or you're a loser', gym leaders got fired if they didn't demolish enough challengers, people waste their whole lives chasing a goal they can't master, etc). Ash's league loss was a farce based around the bad hubris the region had given him, and no one having any sympathy for him or his Pokemon not performing at their best capacity because of some 'excuses' like being kidnapped and exhausted by criminals.
I think Ash enjoyed the Kalos region, especially who he was traveling with.
