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.
Not sure why you think there is no structure? I take him to my training area 3 times a day on a long line or leash to work on OB. I spend time at every feeding, walking or turnout mastering "Wait". He gets one hike across the farm every day. It's his only "free" time. Besides that, he is kenneled. He isn't ready to live in the house yet. Sorry I didn't make all of that clear.
Lifting him for an Out hasn't worked for the most part. For small things he picks up, it does. For things I have that entice him, it does nothing except fire him up more. I suppose I need to hold him until he let's go, but I don't want to "hang" him when he isn't being aggressive with ne, per se, but just extremely focused and driven. He definitely has a different "eye" than my other boy.
He's really a sweet, happy boy for the most part. Its just that he has had NO training at all, and he seems so driven. Definitely a challenge. So, maybe I'm expecting too much too soon. I recognize that he's my first high-drive dog too, and so he's GOING you be different.
Should I not allow him any free time? I felt like a hike was a good thing as long as he stayed close. We mix in some training there too.