Sentimentality can get one in so much trouble.
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Indeed. It can also be harmful at times just handing out money. Some people are in shelters or programs and they are getting help. When given cash they may abandon the help they were receiving for drugs and the street.
I think it is always handy to have a few printed cards of places to get help, shelters, food, and such. Share the good news, offer to arrange for them to get to or contact a source of help. Donate to the places that specialize in this help.