In Red/Blue, it was really easy in the beginning with Bulbasaur because the first 2 Gyms had Rock/Ground and Water types, which were both easy for Grass Types.
Playing with Squirtle gave you an advantage at the first gym, but at Misty's gym Squirtle was useless (cuz water vs water)..although if you caught a Pikachu near Pewter city it wasn't all that hard. And Then at the 3rd Gym they had Electric Pokemon, so you had a disadvantage here, too.
Charmander was the hardest at the beginning. Because the first 2 Gyms had an advantage over you, but after that playing with the Fire Starter was fine.
*sniff* the memories....
