I own 50 acres. I let 8 people hunt there during the gun season. Archery season is off limits for everyone but one of my buddies and myself. For archery season we have a laminated aerial photo with all stand locations marked on it. We have the picture hanging on the back of the shed. Whenever my buddy or myself are heading into the woods we mark on the aerial photo where we are hunting that day. This helps us form ruining each others hunts. We have several stands set up for each wind direction. This gives each person a stand to hunt on any given day. The key is to only hunt a stand if the conditions are right.
As far as choosing who to let hunt on your property. I let my buddy hunt because I have been going to his camp for the past 10 years. Plus, he is a serious hunter who is not going to take any shortcuts and screw up my season. During the gun season the more guys the better (to a certain extent). Eight only hunt the first day or two. Plus we can do a couple of drives with that many people.
eddie