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The problem with this scenario is that we don't really know what is in someone's dark heart. Someone robbing another person at gunpoint is not an individual climbing the socio-economic ladder very well. If you could see into his mind that all he wants is money, that would affect your decision, but you can't.
How many robberies, burglaries, etc end up with a dead victim because one of the perpetrators "just lost it" or "went nuts"? The Cheshire, Connecticut, home invasion murders is a great example.
Violent criminals can become drunk with power they don't normally have and make snap decisions that weren't initially part of their plan.
As far as the down-on-his-luck man-with-a-toy-gun scenario? Is that a joke? You buy the ticket, you take the ride.
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