We have to look at the time period. I believe that it was stated that the writers were only planning the kanto series and then would call it quits. Hench why there were so many pitty badges. Every gym battle that Ash went to he never won on his first try. He either got it for a good deed ( Brock, Misty, and Erika) won by default ( Sabrina was not able to battle cuz of laughter), won after a rematch either through loss or Team Rocket interference (Lt.Surge, Koga, and Blaine) or challenge the right gym but not the true gym leader (Team Rocket). But look at how popular the series has gotten and its to the point that the writers make Ash mad at the sight of a gym leader giving out pitty badges.
On Nov 21, 2010, I'm going on vacation. I'm going to a country to visit two friends and a grumpy oldtimer who are awaiting my return.