<p>My concern would be him not handing in his work on time. That is not going to fly where ever he goes to college.
The other thing is he is probably going to have to take a least one English class in college and he will also probably have papers to write in other classes. I would concentrate on him understanding there are consequences to him not turning in his work. If you go about the route you are talking about to convince them to raise his grade he may think he can slide by this next year too…its better to get it handled now rather than once he is in college. </p>