I think dropping out of high school is the dumbest thing Bob can do. I have a couple of friends that dropped out and now they're stuck working at dead-end jobs at bookstores. He should get through the couple of classes he needs to get through and go to college, especially if he's good at programming.
As for the problems with a few classes, some complete airheads can get through high school. If he's smart enough to program, hes smart enough to pass high school math/english/history/science...
