Absolutely correct. Ash was irresponsible. I'm not saying that the Kanto starters would be much stronger than Pikachu, but if Ash woke up on time, he would've become a much stronger trainer to begin with. Team Rocket wouldn't stand a chance against Ash if he'd chosen a proper starter.
Also true. I actually think, in every season, he grows younger. Besides that, Ash never learned anything, imo.