But see none of that explains the lack of results though. If whether he wins or loses is inconsequential (which is the conclusion I would draw from the "its about the journey rather than the destination" which is an excellent analysis of the shows formula) than why not have him win a regional canon tournament. I understand that your trying to offer points as to why this is so but what im trying to get across is that there is no rational point. Yes Ash's defeats are meant to help buildup leaving for another region but that was my point with the Orange Island example. He was coming off a huge victory and by the time he lost Charizard, he was back to square one. I mean it happened at the end of the Battle Frontier too. So the series has shown the ability to easily transition from Ash winning to starting all over again. The fact that they've only done this twice in 14 years, is kind of sucky for long time viewers.
"If that's what it means to be wise, I guess that means I'll be fool all my life" - Naruto, after Jiraiya has told him to wise up and give up on his friend.