Well rules are rules and if he has repeatedly broken them wether it was because he shot his first buck, second buck , whatever, then I would not let him hunt. You are trying to better your hunting and he is disregarding your work efforts and direct instructions. If he doesnt get it right from the beggining then whats going to happen if you try another management thing like shooting does only, or what have you, judging from his past mistakes he's just going to do whatever he wants again.The worst part about this is he is your buddy, you are doing him a huge favor and now you are the one that has tomonitor and babysit his actions.

I would take his past actions and call it a lesson learned, the question is have you learned your lesson or not???