A few quotes from the Rabbi on 'Tzedakah and Healing'
in which he explains the reiteration in "Give to him readily" as giving with a good heart
Some people give charity out of shame, when they see wealthy people offering coins to the poor, for example. The dignity of a person who does not give, however, will be compromised. He gives for this reason, because of shame, so that his dignity not be compromised. Then there are those who give charity to the poor because of their complaints, fearing that the poor might complain to them and curse them… In all such cases, they do not give with a full heart, and because of this it says "Give to him readily", meaning to say – there are two gifts: one from the heart, and one not fully from the heart.
Yismach Moshe, Sermons on the Torah, Part B, p. 293 – 294, Jerusalem 1989