I am politically pro-freedom, which means pro-gun, but I find this entire thread highly disturbing. The whole idea of someone, anyone, intentionally passing through an area where they are expecting trouble is utterly idiotic. Just because it is the most direct route does not mean it is the only route. Plan an alternate path, or find an alternate means of transportation. Your life isn't worth riding your bike.
If you do decide to begin carrying a firearm, you need to do a lot more than just obtain a concealed weapons permit. You need to search your own soul for what you think you are truly made of. You just don't know until it happens. If you pull draw your weapon, you better be prepared to use it. If you are not prepared to use it, don't bother packing it.
Of course, the irony in all this is that you won't really know until it happens, and then it is too late. If you tell yourself you can do it, and you find out you can't, you are going to sustain serious injury or get killed when you may have only gotten smacked around a little and robbed in the first place. If you are going to pose as someone who resists with deadly force, you need to be willing to show your cards when a street-wise assailant reads the fear in your eyes and calls your bluff.
For what it is worth, most people freeze up the first time they are put in a situation like this, and that is after hours of training. It is extremely unlikely you would keep your composure and retaliate with any illusion of smooth execution. More likely you will be laying on the ground pissing yourself.