How many times? How does one know when it is 'time'?
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Until the dog is no longer afraid of the shot. If you have a dog running making chase on a flushed bird, I think it's a clear indicator that it is time.

Personally, I wouldn't mess around with pots at this point. The owner needs to see what the dog is made of. If he has the desire, it shouldn't be a problem. If not, it'll be a nice house dog.

If the desire isn't there initially, I would throw a flightless bird on the ground and see what the dog does with it. If he wants to hunt you should be able to get through this.

Good luck