RE: Let him hunt or not
I've had buddies do all kind of things tome that would be rude and unthinkable in any other area of life but for some reason with hunting they think it's ok. One time one friend who's property I was hunting on put a guest on the only stand I had on the property, one that I owned, had cut the trail, hung the stand and seen deer on. I was entering the stand a little late that morning (traffic) and I see someone I don't know in the stand and I back out and hunt on the ground. We had words about it because (1) I had told him I was coming that morning and would hunt that stand, (2) I didn't know how safe this guest was and he could have shot at the noise of me entering the woods. He didn't understand why I was upset. We didn't speak for over a year but I finally decided to let it go and we've hunted together ever since and he's even more considerate these days than he ever was.
My other buddy is just socially clueless. He is just unaware how much he annoys others with his competitive spirit and selfish ways. He will always take the new water when fishing, best area when hunting and just generally isn't considerate. But I've known him thirty years and have given up trying to change him. I enjoy hunting with him when he comes to hunt and just focus on that aspect and let him have his choice of stands. Sometimes I just want to hunt to be hunting with friends and not just to kill the biggest buck.
I'd just tell him to buy one stand, hang it, and hunt it. Volunteer to help him figure out where to put it and tell him what size restrictions you have and why. Unless he's clueless he should get it. If he's clueless, well decide if you want him in camp or if you want someone who is going to toe the line.