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You want to stroke a 351w? You could stroke the 302 and get more cubes and a little more power.
Personally I would give him one with a 302 and have a another 302 as a spare. The limited power will be good for saving the drivetrain and the other engine will swap in when he over revs and blows the other one up. If the 302 doesn't have enough get up and go, I would change the gearing to 4.10's or higher. He can run big tires and give him lots of low end grunt, and this would limit his top speed, which as a parent I think I would want to do.
I think he's responsible enough to figure out that to drive the truck, he needs to keep the drivetrain together...and keep the law away I know he's gonna get into a few street drags at one point or another, but teenagers will be teenagers