Well, it sounds like you have been doing your homework, (Good for you!)
I have personally never used breeding hobbles, although I have considered it. For an unexperienced stallion (and I consider yours to be unexperienced, one baby does not make experience) I like to use 3 people to hand breed. You need an area small enough for confinement, yet large enough so that the handlers can get out of the way if necessary. I use one person to hold the mare, another to hold the stallion and a third to, well to put it delicately, be the "helping hand" if necessary. Some inexperienced stallions have difficulty finding the right "spot" and need some help. Obviously, the stallion must be very calm to do this and be very used to having his "equiptment" handled. If he has a problem with getting his sheath cleaned, ie kicks at you etc, DON'T help him. After his first breeding season, I would have 3 people "on hand" but you will probably only need two.
We both pasture breed and hand breed. (pasture breed our own mares, only hand breed outside mares) We have looked into AI and our vet will collect if necessary, but we haven't had the need yet.
I hope I answered some of your questions.