Here's the problem with Ash winning (i.e. getting first place) in ANY of the Leagues:
If Ash wins one league and not the next, there's gonna have to be an explanation as to why, and as the writers don't like to imply that Ash wins/loses his battles by luck, then:
One explanation would be that he slacked off after winning and got overconfident, which would actually be a good plot point and good char development, but the writers would actually have to remember to write the entire story up to the next region's league with Ash training less or having a visibly weaker team or something likethat, which would be difficult, and moreover, the writers have already established that Ash can be a slacker in everything EXCEPT Pokemon training. So that wouldn't work.
And if not that, then:
Another explanation is that the trainers of the region with the League that Ash actually won are overall worse trainers than other regions' trainers (which we know is not true of Hoenn, what with Harrison), and this will disappoint/anger a lot of Hoenn fans.
