I had the same feeling. I think it's because, as a reader, I am unconvinced that the guy is deserving of more money. He might be, or he might be one of the many homeless that have basically chosen to be homeless. My default is to suspect the latter, so his statement comes across to me as better enabling this guy to milk money out of people. Mind you, he might truly be in need, but the article does not demonstrate that. It merely assumes that giving money to the homeless is good, which I disagree with.

Note: Helping those who wish to not be homeless I support; but I don't think that simply giving them money will achieve that.