RE: Let him hunt or not
Been there, done that. Ist shots/kills you can be forgiving-we all think any deer is a giant the 1st year or so.
If you are true friends you should have no problem sitting down & explaining how you want YOUR land managed for Deer. Put him in the less traveled Deer area, hang his own stands since he has the time & maybe he will learn what Bowhunting is really all about. You LEARN by DOING.
You may find he can give you tons of information on an area you think is not so good. Let last year be last year but make it VERY clear this year on your feelings. Friendships are like marriages-you let the little things go & pretty soon they fester into that big "D".