Arrow,
Will this guy listen to you and take your advice to heart?
If so......
Take him back to Hunting Ethics 101.
* it's not OK to wound multiple deer until you finally hit one well enough to kill and recover it. That's just plain wrong.
* practice so much that you know how far you can shoot accurately, and never shoot beyond your ability. Never take a "maybe" shot regardless of the distance.
And so forth.
Sounds like this fellow is so eager to get a deer that he will take any shot he can get instead of disciplining himself to wait for the high percentage shot. He needs a seasoned mentor to emulate.