(Somehow this half of my post disappeared)
As before and regularly it seems, I agree more than disagree. But when I considered myself a conservative I had to really wrestle with his words of give to those who ask. I justified not giving to a person in the street using that same thought process you presented and not wanting to enable wrong behavior. I sometimes suppressed some really strong, overwhelming urges to give on that same reasoning.
But Jesus said give to those who ask. Love the neighbor and give him or her aid regardless of how unable I am to know what they have done or will do with their life. Jesus did not to give only to those who show themselves worthy. He said give to those who ask.
I am now convinced at least some of those times I was suppressing the urging of The Holy Spirit. I am not responsible for what they do with the money, but I am responsible for giving when asked.
I do try to give responsibly. If they are asking for food and I have some or there is a restaurant nearby I give them actual food. If they need gas I buy a tank of gas rather than just a couple of bucks that get them no where. I also learn where nearby shelters are and who runs them so if they are trying to get to shelter I can help them.
But if I really do believe in individual responsibility and Jesus said to give to those who ask, I will at least do what I am responsible for. Then they are responsible for what was given.