So how do any of us know that the guy on the street asking for money actually IS homeless? I mean, if we're not stereotyping, of course.

I see less fortunate people on the subway and the streets all the time, and it breaks my heart. I never give directly to them, but when I see someone begging on a street corner, I always make a mental note to donate to charity. By doing so, I know for certain that my money is going to support a charity that will help provide these people with food and shelter. Plus, my company matches charitable contributions, so my contribution goes further.