Ok, bear with me here... but for some reason I could actually see Satoshi winning the Higaki Conference.
Personally, I don't believe Satoshi actually deserves to win but logic isn't an issue here. I think the way things have been set up he actually does stand a fair chance from a writers POV. Here's my theory:
Satoshi got through Isshu quick, second only to Kanto time-wise. The reason for this I believe is so Satoshi can go on an Elite Four quest... it's already been established that Isshu has a Champions League, so we know the Elite are waiting. I've always reasoned that if Satoshi was to go after the Elite Four he would have to visit them at different sites similar to the Battle Frontier. Also, don't forget that there's nowhere set up in the games that Satoshi could reasonably go after. I doubt he's going to waste a year trying to make an awesome movie at PokeWood and I don't think the writers would create a league again... but having said that, Satoshi's challenging the Elite Four and winning allowing him to face Adeku would be similar to the Orange League.
Also, there's enough leftover locations from BW2 that Satoshi could travel to... Black City/White Forest, Hiougi (Aspertia) City, Sangi (Floccesy) Town, Yamaji (Lentimas) Town. Any of them could be used as E4 waiting places.
Also, there's the question of Iris... it's been established that Iris is being considered to replace Drayden as Gym Leader so when Satoshi leaves Isshu then Iris could reasonably stay behind when Satoshi heads back to Kanto.
Finally, the opening shows all of Satoshi's older Pokemon. If they're going to be added to his rotations, surely it would be good for him to do it while facing the E4. Also, the final episode of D&P (slightly) hinted at Satoshi getting a match against Shirona... ok so it'd probably be Adeku but still, getting a shot at the Champions League is the next logical step for Satoshi and even if he didn't win I'd still feel satisfied that he was slowly but surely improving.
So, Satoshi winning the league... thoughts everyone?