Alright, We don't know if Ash will win in Alola. He was so close this time and if the writers agree with most of the community, They"ll probably make him travel to Alola with Serena. Personally, I think he'll travel to Alola and Meet Sun (The female protagonist of Sun and Moon) but thats just speculation.
I see many comments addressing their opinions on Ash winning in Alola. If he wins, They'll have to use a new character as Ash has already fulfilled his dream of becoming a Pokémon Master. That being said, Ash may decide to continue his journey even if he does win... What if he wants to keep traveling to diffrent regions to experience new things and meet new Pokémon?. Knowing Ash, Thats something he'd want to do. Personally, I want Ash to stay... He's been with us for a really long time and thats what matters.
If you're a long time Pokefan like me, You would probably want Ash to stay. I like Red more then Ash, But Ash is an amazing character too.
The point of this post is to tell you guys my opinion on all of this.
Do you want Ash to stay?
What do you think will happen if he wins in Alola?
Tell me!