Here are some quotes from the Church Fathers and from some teachings regarding almsgiving.
Mercy to the suffering is greater than fasting. The Church reads Christ's words on the Dread Judgment on the Eve of Great Lent, so that the faithful will know that the main Lenten struggle is to have mercy on the unfortunate. For I will have mercy rather than sacrifice (Hosea 6:7).
To do alms is a work greater than miracles. . . . To feed the hungry in the name of Christ is a work greater than raising the dead in Christ's name. …When thou work miracles, you are God's debtor; when you give alms, God is your debtor." St. John Chrysostom
God sells righteousness at a very low price to those who wish to buy it: a little piece of bread, a cloak of no value, a cup of cold water, a mite. Abba Ephrem
Through the cheap price of doing good to men, we can acquire the priceless Kingdom of God. Philaret, Metropolitan of Moscow.
The bread you do not use is the bread of the hungry. The garment hanging in your wardrobe is the garment of the person who is naked. The shoes you do not wear are the shoes of the one who is barefoot. The money you keep locked away is the money of the poor. The acts of charity you do not perform are the injustices you commit.
St. Basil the Great
"Lift up and stretch out your hands, not to heaven but to the poor; for if you stretch out your hands to the poor, you have reached the summit of heaven. But if you lift up your hands in prayer without sharing with the poor, it is worth nothing ... Every family should have a room where Christ is welcomed in the person of the hungry and thirsty stranger. The poor are a greater temple than the sanctuary; the poor are an altar that you can raise up anywhere, on any street, and offer the liturgy at any hour." St. John Chrysostom
"Do not grieve or complain that you were born in a time when you can no longer see God in the flesh. He did not in fact take this privilege from you. As he says, 'Whatever you have done to the least of my brothers, you did to me'." St. Augustine
St Lawrence was questioned by a pagan governor who had heard that the Church had a large storehouse of riches and wanted St. Lawrence to give them over to the governor. St. Lawrence told the governor he would show him the storehouse of riches. He took the governor to the slums and pointed to the poor, the lame and the ill and said, “These are the treasures of the Church.”
The world is fallen, and there are liars and cheats out there and we are called to go the second mile, turn the other cheek, give the shirt off my back to those who only ask for my coat, lend without expecting re-payment. Is that being gullible? No, not if you are doing it with your eyes wide open; it is being obedient to the gospel. Wise as serpents does not mean tight a drum... it just means we know the score going into the game, that the deck is stacked against us. And like Jesus, we “play the game” to lose our lives, not save them; to give, not keep; to bear all things, not avoid carrying dead weight; to believe all things, not be suspicious; to hope all things, not be pessimistic. So, yes, once in a while we inadvertently give to someone who really needs and appreciates it, but regardless of that, we need to give, on purpose, not by accident, and without judgment.
"If you help a poor person in the name of the Lord, you are making a gift and at the same time granting a loan. You are making a gift because you have no expectation of being reimbursed by that poor person. You are granting a loan because the Lord will settle the account. It is not much that the Lord receives by means of the poor, but He will pay a great deal on their behalf. 'They who are kind to the poor lend to the Lord' [Prov. 19:17]"
St. Basil the Great.