Hopefully, he'll at least make it to the Top 2. He's come a long way.
You Might Be A Redneck If...
You think The Nutcracker is something you did off the high dive.
You've ever smuggled food out of an all-you-can-eat buffet.
The original color of your carpet is an unsolved mystery.
You've had more court dates than second dates.
The closest you've come to royalty is eating at Burger King.
You've ever stared at a carton of orange juice because it said "concentrate."
You think a quarterhorse is that ride in front of K-Mart.
It'd be interesting if he got to the final this time around. I'd love to see him go home with the number 2 position. Either that, or that he wins the league and gets to partake in an exhibition match with a prominent member of the competitive battling scene.
I'm pretty sure the original DP plan was to have Ash win the league and face the E4 either losing to them or Cynthia. Ash could win Kalos and the next league but lose the Gen 8 one and I'd be ok. It truly matters how well he trains his team and if he uses older pokes like in Sinnoh. Not only did he have good Pokemon but he had better strategy which helps
If the writers know what they are doing, it is logical that he should either make it to the semifinals or win in the Kalos region due mostly in part to the ever closing gap between generational release dates. While I don't think they will ever come faster than two - three years apart, this closing gap makes it so they can't continuously rewrite the character as there isn't enough time to garner entire new generations of fans with such a limited time. It is likely that they will have to move away from Ash within the next three generations due in part to this as well. How I see them utilizing this time is to have him in Kalos lose in the semi-finals, win in the Generation after that but fail to beat the champion, and finally win against the champion in the 3rd generation from now while also having him play the mentor role in that generation in order to gently break in the new character.
At least that is what a writer that can see the tipping point would do. Though judging from what occurred in Best Wishes... it is likely they don't see this coming.
From the research I did, it seems that he's always in the top 4-16, so based on that, it doesn't seem likely, though it would be nice to finally see him win. I mean, the last time he won, all the way, was Orange Islands.