Oh yeah, let him bring the gameboy.  I bring mine!  One of my fondest camping memories was at the end of a long day.  Camp set.  Fishing from shore.  Enjoying a smoke.  Playing a turn-based gameboy game with my buddies.

This is a trip for him to enjoy and for him to get hooked on.  Let them pack the kitchen sink if they want.  Best way to learn what not to bring is to carry it over a few portages.  Chores yes, schedule no.  Chores must be done before bedtime.  Otherwise, being on your own schedule is what it's all about.  Best way to learn that shelter goes up first is to have your gear rained on.    :D

Alternate is to claim the bottle doesn't open until the work is done.  14 is old enough to have a drink with the old man, isn't it?