The Visiting Teaching message for this month is on Becoming an Instrument in the Hands of God by Caring for the Poor and Needy. While talking to my visiting teachers the other day we got into a semi-debate about the best way to give money to the poor. One of my visiting teachers said that she doesn't feel comfortable giving money to random people she doesn't know...random people on the street. You never know what they'll do with the money; drugs, alcohol, worse? She feels better about giving the money to the church. That way she knows that all of it will be used for good. While I definitely find the merit in that point of view I also think there is more to it.
Jeff Lindsay also recently commented in this topic. He believes in what he refers to as social gambling. "Some are going to waste it. Some are going to lose it. But for some, that gamble you took could turn into a jackpot that could make a huge difference for that day, that week, of even for a life -- the difference, perhaps, between hope and despair." Even if your money only helps a small fraction of those you give it to it would be worth it if it can make a real difference in that person's life.
Basically, when it comes down to it, it doesn't matter how you choose to give. Just give.