Not a tax attorney or an accountant, but as far as I can determine the gifts would not be considered taxable income insofar as the homeless man is concerned.
Tax Rules for Gifts
By Kaye A. Thomas
Current as of June 5, 2012
The main rules for gifts between individuals are fairly simple. These gifts don’t produce deductions for the donor or income for the recipient. And most of the time there’s no gift tax, either. But if you give more than the annual exclusion amount ($13,000 as of 2012) to one person other than your spouse in a single year, you’ll have some planning concerns — and a reporting obligation. Gifts you receive aren’t considered income. It doesn’t matter how large they are. You don’t report them on your income tax return in any way.