I think it boils down to, there is no right answer and answers that are coming are hard ones to make. I'm not going into my life specifics because, frankly, it doesn't matter. This is all opinion for the most part. I think people are basically good and their hearts go out to anyone that is suffering. I think people that help by giving food/giving money/working towards social reform/etc are helping how they choose to. It might not be how all choose to do it, but they are doing something.
I don't think this is a one-up-game. There are times I give money and there are times that I can't put enough in my budget to make ends meet. There are times I've needed money. I lived in a state that people made six figures a year panhandling (I'm not saying homeless just the act of panhandling). Sure there are studies about it, but people in this vein aren't robbing people. This is money handed over to them.
Sure, maybe it's under false pretenses, but there is a lot in life that is like that. We buy a laptop for X amount of money and then find out that the next year the operating system doesn't work. We made that choice. We take a salary position and then we work out how much we actually make an hour after we see how many hours we put in. We made that choice. Or you think benefits are included and aren't. I know these are not on the same par as homeless or panhandling, but they are decisions we make with our money. If you give money to a panhandler. That's up to you. If you give it to the state to try to win the lottery that's up to you.
If they are using it for drugs. They are using it for drugs. If they are using it just to pay their bills or because they found a way to make six figures a year. More on them.
I'm likely to give my time and my money to organizations helping the homeless or my real heart of hearts is women (and men) fleeing domestic violence. This doesn't make me a saint or sinner. It just makes a choice I make in life. These are hard topics and the right thing is a hard thing to know or to judge because people have things that have happened in their lives to form their personal choices. You can't know them. I don't think you should judge them. I just think you should know that most people are helping how they can and how they feel comfortable.
This is however, just my opinion, so you can take that as you will.