This is a question, I have been wanting to ask people for days.
In the last episode of Best Wishes, you see Ash saying this dialogue in a somewhat disappointed tone. Now usually, you see Ash feeling bad about losing a league but he usually forgets about it and only talks about the next journey. But at the end of Best Wishes, for the first time you see him look a bit disappointed.
And that’s not it, even in the concluding episode of the league, you see him say “Best Eight huh…” (In Japanese version).
Is it just me overthinking or does Ash feel worried about taking a step back from his Best Four rank in the Sinnoh League?
He also apologized to Ookido about it at the beginning of Episode N:
I wouldn’t say he was worried, but he indeed acknowledged (meta-wise, too) that it was his first counter-performance in a League. Overall, I think it depends on the way you’re looking at Best Wishes! as a whole, and how Satoshi handled his relation towards Pokémon? He reached a really strong status, during Diamond&Pearl, with a team who suffered a lot all through Sinnoh: it was straining, productive, yet potentially noxious at the same time. In Best Wishes!, the focus (as a series, and as Satoshi himself was interacting with people - he could have been way angrier at Shooti, for example, but let a lot of things slipped, as if he didn’t want to get angry) was more on the time spent with Pokémon. Satoshi initially came for vacation, after all, and the journey was, although predictable, decided after his arrival. Best Wishes! appeared as an appeasement, something, maybe, to go back at the core of what Satoshi said he cherished the most: a partnership with Pokémon where they would have an equal status. More communication but less stress; less emulation but more openness? (Personal opinion, though, this is my way of conciliating meta-intentions and Satoshi’s intention behind his behaviour.)
We did have a proof with the League that, although Isshu’s journey was more peaceful, contained maybe more… happiness?, it didn’t make Satoshi and his team as powerful as in Sinnoh. But at the same time, it showed that Satoshi was still able to reach an honourable level without having a “competitive” journey? He didn’t have any “main rival” either in Hoenn, where he reached the same level as in Johto/Isshu, but he was Haruka’s mentor, so put in a responsible role, a guiding figure. In Best Wishes!, Iris and Dent were both more experienced (given how Iris was already shown fighting as a child) and Satoshi didn’t have any responsibility towards them, nor anything to prove to anyone; his rivalries were, overall, all friendly (I wouldn’t say Shooti was a “main” rival given that his story was tied to Adeku and stayed that way: there wasn’t any personal rivalry (like with Shigeru) nor “professional” one (like with Shinji) until the end; he was more indifferent than defiant). Satoshi, in Best Wishes!, was “free” of any pressure.
So, as I see it, Best Wishes! was about appeasement (in Satoshi’s behaviour from the start, and as a development for Iris, Shooti and N), strong interactions and communication issues/resolution. It wasn’t a “stage”, it was made of mini-arcs standing on their own. Best Wishes! ended while saying we would go to something else:
… Maybe a more competitive/”responsible” saga where Satoshi would take the lead, after feeling that he had relayed too much on his Pokémon without returning the favour during Best Wishes!? It wasn’t the first time that the end of a series was introducing a different “spirit” which would blossom in the next one. (I wouldn’t say it’s a retcon, I would say that, the way it is presented each time, it is assumed that Satoshi put himself in a different state of mind before each journey, with different intentions and expectations.)
I thiiink that what was what acknowledged is that Isshu’s journey wasn’t negative, but not sufficient enough or, more precisely, incomplete on the matter of Pokémon-training: while going back to the root of focusing on Pokémon interactions, it lacked a sharp emulation. It was highlighted when N happened: we didn’t see a clash between them which would have forced Satoshi to go higher, Black&White-style, but a story about N coming out of his shell and reversing his system (he was presenting the negative as a norm). And then, there were rivals in Best Wishes!, but it was mostly about sharing and facing things together, as friendly rivals, than confronting each other as respectful rivals. So, now that Satoshi had gone back to do things for himself and his Pokémon, without pressure, he was somehow… acknowledging and readying himself that, to go higher, to actively put his values to use, he would have to go back to being… “sharper”, less intransigent? Hence his resolution, at the end of Best Wishes!, to focus once again on his goal now that he had learnt again to enjoy things without any ulterior motive?
That’s the impression Best Wishes!'s ending gave me, but it's too soon to confirm it in XY ^^’