Bonecrusher is right, heading dogs are little bitches with stuff like this.
I'd say don't use the .22, the sound is to sharp for them. Shotgun works well with my lot, the young ones stay in the dogbox for several trips and just listen. Even take him to the carpark at the local gun club, don't take him in just sit out there talking to him in the car for half an hour. If he's comfortable after that leave him in the car and go for a wander around...
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