A few quotes from the Rabbi on 'Tzedakah and Healing'
in which he teaches to give twice to the poor person, once to appease his suffering and once to fulfill the commandment.
"Give to him readily and have no regrets when you do so". I once saw a man, the greatest person of his times, approached by a poor person originally from a privileged background, who shared his suffering with him. He gave him a proper donation, and then gave him a second one. This man was asked, "What is this, Master Rabbi?" His reply was that the first time he had given to ease the poor man's distress, because of the suffering he had described, and that the second time was for the sake of the commandment. This is what the verse says, "Give to him readily" – meaning to say, twice, and then "have no regrets when you do so" – that is, giving should not be done out of your suffering heart or pain, for then the commandment will not be entirely fulfilled; give for the sake of the commandment.
Likutie Nissim, Parshat Re'eh, p.273, published by the author, Tel Aviv, 1971