I think the video also says that we should only command out once a day so how do I get around this. I suppose this won't be as much of an issue in a few months but for now I would love to hear opinions on what is worse outing a couple times a day or letting my dog chew his prey item in the crate?

You dont have to follow everything to the finest detail.
If you dont want to out your dog to get the prey item off him before he gets in the car then simply lift the dog by his collar of his front legs until he chokes it out, then kick it away. Now put your dog away. This will leave the dog wanting the prey item which is a way of promoting his prey drive.

Alright, this really isn't too difficult here.
Things that you can do to get your dog to out at/ or by the car:
Have a bowl of water out by the side of your car - often after a training session, the dog will drop the item to take a drink. At that second, immediately heel your dog away, making sure you control him fast enough to prevent him from re-biting the object.
Or...
You can simply put the dog back into drive for another item, by teasing him - The Flinks video's demonstrates this well. When the dog drops the item in his mouth to start biting the newly offered item, continue the teasing and circle away from the dropped item that's now on the ground. Then put away the new prey item and take the dog to the car.
Or....
If we're taliking about protection and the dog won't out the sleeve, have the helper come up to you with a new sleeve on - when the dog outs the current sleeve to start barking at the helper, move away from the outed sleeve on the ground - the helper than runs away ( the frustration that the dog feels here is not a bad thing ) and you put your dog into the car/ crate.

Obviously, all the above outs take a little smarts on the part of the handler - if you out the object between the dog and the car/ crate, and you have to pass by that stationary object on the ground again, do *not* allow the dog to gain control of the object again!

What about dog winning by chasing decoy off?
You out the dog, keep him close to sleeve (but not close enough to bite it, or bite the decoy) and let decoy grab sleeve and run away like he is really scared.

It might depend on the dog, but it worked for boosting self esteem with some dogs (especially when we worked on small area, and dog would chase me out of yard and out of sight).

I have seen tapes where dog is given _one_ bite (close, back bite on jacket) over several training sessions, outed (choked off) and decoy ran off screaming like girl. Next time dog was all over him.

and decoy ran off screaming like girl

There are two dogs at our club that make me consider that action every time I suit up! <img src="/ubbthreads/images/graemlins/laugh.gif" alt="" />

I know what you mean, but credits go to decoy in this case not to the dog (pup really,um, whell only ppl that are into working dogs would call that pup <img src="/ubbthreads/images/graemlins/smile.gif" alt="" /> )