Rav Dovid Grossman
Answer: Whenever one is approached by a legitimately poor man who is asking for tzedakah for himself, he has a Torah obligation to give him at least a small donation. If one is unsure if the man's story is legitimate, it is a safek d'oraysa and he should be stringent and give him something. When one is determining to whom to give a larger donation, one should do his due diligence and give more to the person whom he feels is more deserving.
The Gemara in Bava Kama relates that Yirmiyahu was being harassed by certain individuals, and he cursed them by saying that even their good deeds should not help them. The Gemara explains that he was saying that even when they give tzedakah, it should end up by unworthy people.
Rav Elchonon Wasserman hy"d explains this Gemara by saying that there are two possible reasons why Hashem makes people poor. Some worthy people are made to be poor in order to give others the great merit of helping them financially. It is a great mitzvah to help these people. Others are made to be poor as a punishment for their sins. Hashem wants them to be poor because of their wickedness; therefore, it is actually improper to help them. Yirmiyahu was cursing these men by saying that their tzedakah money should go to this category of unworthy paupers.
If we are supposed to give tzedakah to the first classification of poor people but not to the second, how are we supposed to know who is who? The Pnei Moshe says that we can often determine if a poor man is worthy of our charity by viewing their attitude towards collecting. If a poor man asks for charity in a humble way, he is probably a credible person. If he is demanding and obviously rude, he probably is unworthy. While one still has an obligation to give a small donation to every ani that approaches him, one can use his own judgment to decide which one falls under which category and, accordingly, which one deserves a larger donation.
As a final point, the Gemara says that we should be thankful for dishonest men because they save us from sin. If someone refuses to give a donation when asked, it is a terrible aveirah; however, because fraudsters exist, one has an excuse for not giving, as he can claim that he thought the man was lying and was not truly poor.
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