sounds like he has a ton of freedom. I don't know that outing at this point is going to be successful when he has basically no structure or rules(according to your description of his life right now).
I personally don't really teach an out at this age, I'd lift the dog til the out(maybe verbally mark it when they do with the word you'll use for the command) and keep the pup in drive when training.
"LEAVE IT" is a different scenario. That command means now, and corrections are involved if the dog doesn't do it. BUT the dog needs to know the command before ever getting corrected. So teach it in a lower state of drive, with a piece of food or toy, with a verbal wait, leave it, then mark/reward when dog complies. Reward with a different treat/toy than what the dog was enticed with. I'd keep him on a long line while you are training and proofing this.
Last edited by onyx'girl; 06-14-2014 at 11:15 PM.