Sorry it took longer than expected to get back to you, you said "It doesn't matter how much money you give them, they are poor, and their lives are garbage."
I would agree if money solved the problem we could fix the issue. On the other hand these people are making just enough to pay bills, never have a dime for pleasure, so of course they are burned out tired and would do everything to just relax or find a way to seek enjoyment in life. I know several people in this category that live paycheck to paycheck and can just barely pay the basic bills they have. If they get a job they lose the government benefits and now must pays taxes making them poorer than living on the government. Or others who make just enough to be over what the governments bare minimum of living is so they are taxed, and now make less than they would have if they just took the governments money. So the system we have benefits those who do not work, over those who barely make enough money.

You also said "Having worked with homeless, I know the extents an organization has to go to feed these people."
I live in a city that it costs more money to get the permit to feed the homeless than the meal. Plus it is now so restrictive that they can not just go hand out food or they will get fined, not to mention they can only go out certain number of days in the year. The bag of lunch they had out to the homeless contains a a sandwich, some fruit and something like a bag of chips. Last I had heard anything on it. That is not enough food for me for a lunch, I am underweight as it is, and that would contribute to me losing more weight if that was all I ate.

I agree there may not be a perfect solution, but reducing or not taxing the poor would be the only other way to make a system encourage working. Since the poor are the people who we are trying to help out. This is why I do like Dan's proposal and see that it could actually work, so long as they don't change the tax codes to affect people receiving that money.