The following is, perhaps, the best article I’ve ever come across on the topic of almsgiving for the homeless…Pres. Candace
We meet homeless people nearly every day on our life's path; people who are often contemptuously called “bums.” We see them at the train station, near the subway, in town squares and parks, and of course, at the churches, asking for money. Each time we see them, our hearts deliberate painfully over the question, “Should we give them alms, or not?” Then, other questions immediately arise, “How much? How should we give them? Is there any sense in giving at all?”
People are generally divided into two groups. The first are those who give according to their means to all, without thinking about it or asking any questions, following the Lord's words, Give to him that asketh thee, and from him that would borrow of thee turn not thou away (Mt. 5:42). The second group is of those who do not give money to “bums,” considering that we mustn't indulge the “bum mafia,” for we participate in their sin of drunkenness and sponging, lying, etc. by giving money to them. These people are ready to fulfill Christ's commandment and are willing to help people, but only those who really need help. They cite the words of the holy fathers in support of this—that the greatest virtue is discernment, for fasting, prayer, alms, or any other virtue will bring a person no benefit if done beyond our strength or out of season. Truly, no one would give anyone money for a rope to hang himself, no matter how tearfully or insistently he begs it. That rope could be a bottle of liquor, which strangles the neck of the beggar each day with increasing strength, or the rope of lies that you would indulge by giving money. There are hundreds and thousands of such ropes.
So what must we do to fulfill the commandment of Christ and please the Lord in the best way? The answer is simple: love. Try also not to do anything without love. Then everything will settle into place, and even the question itself will seem silly. As we know, Though I bestow all my goods to feed the poor, and though I give my body to be burned, and have not charity, it profiteth me nothing, (1 Cor. 13:3). Of course, it is hard to just up and love every homeless person, but it is usually quite possible to show compassion for every person that the Lord has brought to us. I would like to share a little practical experience in helping the homeless under various circumstances.
For example, you are walking to work, and a tipsy beggar asks you for money. What should you do? Don't be lazy—ask him why he needs money. They are often asking for food. This is the simplest case. Then you need to go with him to the nearest grocery store and buy him something he hasn't had for many long years. Give him a holiday, as if this were your old classmate. Something tasty and filling, like good sausage, chicken, cheese, yogurt—in other words, something that they could never get for themselves because it is too expensive to eat in sufficient quantities. Even if the homeless person was lying to you at first about food, he will nevertheless be thankful. Try to transfer this thankfulness to the Lord, let him thank the Lord, and not you personally. For example, tell him that it was Christ Who sent you to him today. Then it will be both bodily and spiritual alms. Try to see a deeply suffering person in him; and if you cannot see in even the last ”bum” the image of God, perhaps very soiled, clouded over, but nevertheless the great image of God, then perhaps you need to discuss this with your spiritual father and pray about it.
Ask the homeless person what his name is, where he hangs out and how often, when is his birthday, is he baptized. Be sincere and kind with him. Homeless people are very sensitive to insincerity. Do not hasten to judge him. We do not know what we ourselves would be if the Lord had deprived us of His protection and hadn't guarded us from the demon of drunkenness and other vices. Wouldn't we be much worse than that person? In a word: love him. Love him to the extent of your heart's capacity; love him sincerely, for Christ's sake. And if even a little love is born in your heart for this person, then the next time, when you are leaving your house, you will probably be prepared for another meeting with him: take some food from home, some warm clothing, a book, or something he might like. You will leave fifteen minutes early for work and find him; wait for him, call him by his name, show some concern for him, and increase love in this world, the lack of which is felt ever more sharply. Thus, from day to day you can live for the sake of Christ, taking care of one poor person. Do not just buy yourself off with money, do not limit yourself to one-time help. It is good, but it is not a perfect fruit. You can't just love for a half an hour and then forget about it. Continue reading here: http://www.pravoslavie.ru/english/42177.htm