And to think, he's done all this in less than a year.

Jokes on you, Ash has actually been taking the fall intentionally for money the whole time. Think about it a minute; how else does he make it to a new region every single time? Why would someone who is a seasoned veteran pokemon trainer (even if time doesn't actually pass for him somehow) consistantly make rookie mistakes that would cause him to lose against pokemon he has a type advantage over? It's because Ash wants to lose because by losing he can make enough money to continue his pokemon journey. Like, he doesn't have a job or any marketable qualities so there's no way that he should be able to afford traveling the entire globe like he does. This also explains why he's slowly been doing better in each league he visits; the higher his spot in the tournament the more expensive it is to buy him out.