I think that Ash is perfectly aware that the title of Pokemon Master is vague and unattainable. He continues to chase it not to gain the title but instead to push himself to continue to get better and have more fun adventures along the way.
Pokemon anime request! Ash’s companions (other than Alola) reacting to his championship win in the Alola league
Misty: Knew from the time at the Orange League that he’d make it, if anything he already did back then. But league being official was just the last step. Still wished he used many of his water type Pokemon.
Brock: He called it the minute Ash forfeit his first gym battle ever. This kid was going to go far. Now if he could just get Kukui and others to help get him some therapy.
Tracy: He was literally drawing Ash’s final league battle from frame to frame. Goes on to make the Pokémon anime series with input from Ash and his other friends across the regions.
May: Knew he’d make it someday, after all, he beat the Battle Frontier. Hopefully he waited to have a big feast until her plane hit Alola.
Max: He finally been able to start his journey. He had just won his first gym badge when the league began. He quickly rushed home to watch the rest with his family. His Treecko and Ralts cheering with him as Ash won it. Of course, he always has a small part of him, guilty for how he treated Ash when they first meet. Boy, if he could go back in time and tell his past self this.
Dawn: Always knew he was going to win someday. She knew Piplup was all for it, plus not having to worry about his Gible’s draco meteor. Just wished she’d had been able to see it in person. But she clearly made that up once he went for the masters tournament!
Iris: Despite their quibbles, she always knew Ash would exceed in Pokémon battling. Now she wished he had more dragon types, let alone used the ones he had besides an ultra beast. But she’s proud either way.
Cilan: He knew it like the back of his hand, like the lines of a cookbook, the station to a train. Yeah he’s basically part of the Ash fanclub and for sure is the co-founder that totally bet Ash would become the best one day.
N: He knew the moment he laid eyes on Ash, that he’d do great things. He’s one of the reasons he can tolerate Pokemon battles, even see the enjoyment and thrill in some cases, but mostly through Ash’s battles. He could defiantly feel Ashs Pokémon’s cheers from all over the region, and perhaps a certain legendary bird or more.
Clemont: He’s a gym leader after all, he could tell from each battle he did whether someone could go far if given the push. Ash was one of those, despite the fact he knew since he first battled him when they first meet.
Serena: Knew he had it in him, and hoped he’d be happy. Also he rejected her and their good friends to this day.
Bonnie: Cheered the loudest, now even more psyched to go on her own journey. Perhaps battle Ash and his mons along the way.
Basing this on if the Alola series was only a couple months since Kalos (since it started as a summer trip) and lasted about a year after, hence why Max is old enough to go on a journey, but Bonnie isn’t.
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Bonus! Rivals (and by rivals I mean actual rivals. Not looking at you Cameron and others I forget. Sorry Gladion and others I know but this is excluding Alola.)
Gary: While he wish he could kick his 10 year old’s butt, but he knows Ash won’t have gone as far without his help. So he better mention him in his acceptation speech. But for real, he’s so proud of Ashy Boy.
Paul: Ever since he heard of Ash beating the Battle Frontier, he knew he was going to become a champion. Not that he’d admit it. No, but he’d totally admit he had the better rival battle out of all of Ash’s rivals.
Barry: Now Ash owes him 10 million more, for he knew Ash would become champion. He just wished he’d battle him for that.
Trip: Ever since he loss to Ash in the Unova league, he’s gone through a big change. Ash showed him what the perfect trainer is, caring for Pokémon and people alike. So yeah, he’s less of a jerk.
Alain: While he wished he got a rematch before Ash made it, he’s glad he did. No matter how much of a odd presence keeps saying Ash was the Kalos champ despite the outcome.
Sawyer: He’s Ash’s number one fan. Of course he was going to become champion. Of course, he wished to battle him again before he done so.
This is how the legacy of Ash Ketchum should carry on:
Ash and friends should be aged up to young adults who have achieved their dreams.
Liko and Roy are big fans of Ash and hope to meet him someday.
On their journey, they meet big names in the Pokemon world (Ash's friends) who tell them all about their journeys with the legendary champion:
Misty is pissed that her (boy)friend hasn't come by or called for a long time.
Brock helps heal their Pokemon and is recognized as Ash's best friend.
Tracey shows them sketches of Ash and his Pokemon throughout the years.
Gary sneers that Ashy boy is just another trainer, but obviously doesn't believe it.
Professor Oak says they remind him of someone he knows.
May, Dawn, and Serena tell them how much Ash taught them about friendship and battling, and how he taught then to chase their dreams.
Iris is mad because she lost a battle with Ash who used an ice type against her.
Cilan tells them how perfectly matched Ash and Pikachu have always been.
Bonnie and Max, who now travel together as teens, talk about how heroic Ash has always been.
The Alola gang talks about how they went to school together and how he won the first Alolan Championship.
Professor Kukui reflects on how Ash became like a son to him.
The stories make them want to meet him even more!
However, he is very elusive, and almost no one knows where he is at any given time.
Eventually, they do bump into him briefly, but he is busy saving the world as usual.
They don't get to talk to him much, but he inspires them to chase their dreams even more.
They continue their journey, hoping to meet him again someday.
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I know they don't want to age him up, but think about how well Legend of Korra went over! They even killed main characters, and the world of Avatar carried on.
Pokemon wouldn't have to kill characters off, but aging them up would be a nod to the older fans and give him ways to fit into the new series in a new way.
I'm still perplexed on how emotionally attached I am to this ship and maybe it's a problem but oh well let me live out my bizzare fantasy that the 0.5% chance announcement of satogou being canon will arrive in my lifetime 🥰🥰🥰🥰
But either way enjoy this masterpiece I have created because I could have not put it in better words x
Leon: Thanks! I was just training some of the fundamentals.
Ash: really?!
Leon: jup. They are really important if you want to stay the strongest.
Ash: that's it??
Leon: of course not. But if the fundament is unstable, you can hardly build anything on it.
Ash: that sounds boring. Can we fight? Please!
Leon: I would rather not.
Ash: huh?! But why?
Leon: I really don't want to hurt you or Pikachu before our big fight.
Ash: what do you mean!? Me and Pikachu are stronger than we look!
Leon: that's true, but neither me nor Charizard would be able to hold back. With all the training that we did I am certain that we would badly hurt you guys.
Ash: that is not fair!
Leon: now, don't look at me like that please. You are a friend and I really don't want to cause you unnecessary harm.
Ash: hmmm…. if I weren't your friend, would you fight me then,
Leon: Ash?
Ash: hey! If I would ask out Hop, would you then fight me?
Leon: hah? Why would I fight you for that! Don't be ridiculous.
Ash: uh, you really look like you want to fight me now.