Ash using weak pokemon is like an athlete training with weights on. When he finally puts together a top tier team, the weights will come off, and Ash will unleash a typhoon of concentrated rape the likes of which the pokemon league has ever seen. Self-imposed limitations have been proven to enhance your ability to improve. Just looks at things like nuzlockes and unevolved runs. Only truly strong trainer complete those. It's coming soon, I can feel it. Ash will have his day.