"To be honest--in either case I would probably just hand over my wallet. I don't carry enough money or credit cards to make it worth risking my life, or the perps. As described, the situation doesn't make me fear for my life.
Does that make me a sheeple?"
Does anyone besides me carry a drop wallet? My real wallet is concealed and my drop wallet has a couple of expired credit cards with the magnetic tapes destroyed, some old business cards I've picked up at various places, 5-10 dollars.
Sit 1. Hand it over he gets nothing of use and it gives me time to get a little space as he's going through it.
Sit 2. Pretend to drop it and get a little space as I draw. If he doesn't bite on the drop.........draw and engage.
Either way he is in posession of my wallet when the cops arrive.