Perhaps there is a threat to Sinnoh that only Ash's old Pokémon can help solve. Some kind of ancient evil that has knowledge of Ash's past Pokémon battles. Ash and his old Pokémon then have to work together to defeat this threat. They might need to combine their old strategies with new ones they learn in Sinnoh to succeed. And along the way, Ash might meet some of his old friends who are also in Sinnoh and they help him in his mission.
It could mean that Ash, in the context of fan - created Pokémon stories (fanfiction), utilizes all the Pokémon available to him within those fictional narratives. For example, he might use different Pokémon for various battles, quests or adventures as written by the fanfiction authors.
There could be many. Some fanfiction authors might create a special tournament arc where Ash has to use all his Pokémon to win. Or a situation where he's in a strange new region with unique challenges that require him to call upon every Pokémon he has in the fan - created story.
Well, perhaps it could involve Ash going on an epic adventure with all of his Pokémon. Maybe they face a super powerful villain that requires the combined strength of every single one of his Pokémon to defeat.
It could be Pikachu. Since Pikachu has been with Ash from the very beginning and is his most iconic Pokémon. It's very likely that in Sinnoh fanfiction, Pikachu would be frequently used as it has a strong bond with Ash and is also very powerful.
Obviously, Ash is going to be the main character. His Pokémon, like Pikachu, Charizard, and all the others he has caught over the years, will also be important characters.
If we consider the common growth pattern in the Pokemon series, Charmander evolving into Charmeleon could be an early evolution in the fanfiction. Since Charmander has a clear evolution line and Ash has a strong bond with it, it would make sense for it to be one of the first to evolve, perhaps due to a tough battle or a special encounter that accelerates its growth.
One idea could be that Ash discovers a Sylveon in a forest. The Sylveon is injured and Ash takes it upon himself to nurse it back to health. This could lead to a strong bond between them, and Sylveon could become a unique addition to his Pokémon team, with new adventures and battles ensuing.
Well, Ash and his Pokémon might get involved in local Alola festivals. His Pokémon could participate in Pokémon - themed contests or challenges during these festivals. Also, they might team up with local trainers and their Pokémon to protect Alola from any potential threats, like a group of wild Pokémon causing chaos in a village.