let's look at it this way, depends on your mindset

when approaching or being approached by a "homeless" person on the street asking for money do you?

a) give him a couple of bucks
b) give him $5
c) give him $10
d) oh dammit, I've gone totally plastic, I'll give him the $25 gift card I just bought for my niece.

when approaching or being approached by a "vagrant" on the street asking for money do you?

a) offer him a ride to the soup kitchen
b) offer him a ride to rehab
c) offer him $20 for raking leaves in your yard for a couple of hours
d) keep walking because you already know the answer to a), b) and c)

So...this poor guy, with a gun, needs your wallet, watch and car keys worse than you do and you willingly hand it all over. Then this crack head, jerk pops you in the belly anyway.

I'd play the odds.