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To the OP.. Happy to read your son came out ok.. even better you helped him understand the power goes to the first person to call 911 (not bring help, as it's already too late for that, but to inform and cover ones position)

This entire discussion reminds me of my standard reply when asked why I feel the need to carry a gun ..
“Crime is random, if you can tell me the time and place of where I will be randomly attacked, mugged, carjacked, I’ll simply not be there and have no need for the weapon”
Same ideal for this…in my twisted mind..
The OP asked “#1 If you were armed, at what point would you draw your weapon and #2 at what point would you have fired ??” And then got all kinds of replies from “shoot him” to “a CHL is not a Batman license”
The simple answer is , well simple.. You shout your warning, whatever verbiage it is for you that you have practiced (for the BG to hear and any potential witnesses) Sir, STOP, ,, STOP, Stay away... If he continues you draw and present your weapon... (all the talk about it not being worth it to stop the theft of an I phone is revisionist history, at this point in the scenario you have no idea if that is the final intent of the attacker)
If the BG walks away you move to a secure place while holstering your weapon and calling 911, if he continues forward and time allows..you shout your second warning “stop or deadly force will be used” if he continues forward you then place two well aimed shots into his chest, while moving to a more secure location and calling 911.
If I knew in advance (see the first quote above) that the BG was just a harmless obnoxious guy that really wanted to JUST use my phone would I draw and shoot him... well no.... but how do you determine what is in a man’s mind and hart as he is coming toward you in an aggressive manner. IMHO you don’t.. you give him all the opportunities you can to understand you will not be his victim, and then you defend yourself using all of the tools you have at your disposal (first and foremost your mind, feet and cellphone).