Dave,
A Whaler is only good for one thing... exchanging horizontal velocity for vertical trajectory! If you're towing a Whaler at 22 knots... behind a 50' Bertram... your son is missing a whole lotta fun.
How is he suppose to follow in his father's footsteps if you don't let him prove a Whaler is unsinkable? Isn't this you in the picture below? Like father, like son...