Well, Naruto present itself as symphatic characther and he is often underdog in start of fight but it repeats same cycle which is; get beat up, try harder, beated up again, and then some freaking reason he then wins by outsmarting his foe (when he should not able pull it off all laws against it from happening).<br/><br/>So, it can get annoying and if it was not for the damn music it would get boring to watch :P. Perhaps the only honest underdog char who does not 'cheat' really is the main char in One Piece. The rubber guy (forgot his name now). he never grows stronger than he is, he just expands and cleverly uses devil fruit ability what he has (which is; make his body function like rubber). Also he depends quite a lot from his group also (where Naruto he only on 'occassion' depends on allies).<br/><br/>Also consider Naruto learned shadow clone jutsu it means it is not hard to learn per se. But more that you need tremendous chakra pull it off. I think in war time academy they have developed varied technique harden the students, increase overall chakra levels and physical fitness etc. So compared to cannon our chars could count as more experienced and ready for real ninja battles.