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Its a great idea. It comes up all the time. Why not give the homeless a little money for working to help other homeless? Unfortunately, the government has placed a huge barrier to entry in front of giving someone a few bucks for an hour of work.

You'd be better off showing them a library computer and introducing them to mechanical turk.

I think that if it is less than $600 per person per year, you can just give cash and there is no record keeping necessary.

But for something like this to work, you'd need to have some type of centrally administered place. I'm not sure what the issues would be with giving someone food for work.