I often encounter these professional beggars (meshulachim) in Orthodox life. They always have a great story. I have a personal code of not giving to people who directly solicit me. Instead, I save my charity for myself. I figure I should pay off my loans from my family before I give to beggars.
I grew up in a converted 3-story boarding house called The Boro Park “Meshulach” House. For those of you who don’t know what a meshulach is, they are those guys who look like Rabbis, and who knock on your door asking for tzedakah for their mothers-uncles-fathers-kallah’s-sick niece. A lot of them are genuinely very poor, but naturally there are some crooks in the bunch.