I think I agree and disagree with
@kyler1945 (never can be sure with that guy.)
If the problem is a true dichotomy (saddle or stand), sure...put him in a saddle.
But there's a lot of kerfuffle, hassle, and fiddle-factor involved in climbing a tree. And people are a lot like dogs when it comes to learning. They suck at learning multiple things at once. Would you try to teach your dog sit, heel, and fetch all in one day? Or would you first teach him to SIT, and once he really has that one down, introduce STAY?
Hunting is not hard, but neither is SIT. In my mind, the first two basic commands of deer hunting you wanna teach somebody are FIND and KILL. Makes sense to me to make that as uncomplicated as possible. Get him in the woods and let him find the sign, and then find the deer. Stick him somewhere and let him take a crack at one he found. Don't have him worried about CLIMB (and all the sub commands that come with that.) Really, I wouldn't even want to start somebody with a bow, because that's it's own can of worms. You can get very deep in the weeds very fast with archery and saddle gear, and neglect the question, "Where are the deer and how am I going to get them from that place to my truck bed?"
All that being said, I have slowly realized that people hunt for different reasons. I want to find and kill deer. That's my reason. I'd burn my bow tomorrow if it wasn't for the fact that some properties are bow only and bow season opens the woods up to me another month, because a gun will kill more deer for me. And I have never and will never climb a tree for any reason not related to killing deer.
But some folks like to shoot their bow. And some folks like to climb trees. Hunting wouldn't be the same for them if they walked around, sat on a bucket, and shot a deer. I'd be thrilled.
If his goal is to become a deadly deer hunter, I think it'd be wise to hand him a stool and a leafy suit. He'll screw up, but he'll learn the fundamentals. And when he hits the point where he feels held back because he can't climb he'll know how to scout, track, plan the ambush, be still, be quiet, get into position, draw, shoot, trail, etc. He wont be learning that and learning to climb.
But, if he wants to climb, let him climb. Some folks like the climbing, the camp life, the camo, the gear shopping, the bow tuning, and all that jazz more than they like seeing a green tint in a deer's eyes, and that's perfectly ok.
Strange, but ok.