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I take issue with the idea that "any" property is replaceable. Personally, I would not consider $5000 cash lost to a thief as replaceable(easily anyway). The robber would have to be seriously threatening me to get away with that amount and at that point, would be subject to my using deadly force.
As far as shooting a retreating criminal who robbed someone else w/o hurting them, that's pretty much frowned upon.
My take was the OP intended to confront the criminal if the threat of physical violence upon the OP's friend was imminent.
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