S.T.
C., my favorite approach (given to me by the mother of three adult men) is to wait until the boy is good and ready (for my sons, it means around 3 years old) and then, on a warm spring day, let them run around the house without anything on. It will take a day or so for them to learn. My oldest never had an accident after that. I put pull-ups on him for naps and to sleep at night. He only needed them for naps for a few weeks and maybe a year for night time. The cheerios peeing game, bribery, new underwear, etc.--none of that ever worked for me. Good luck!