In response to what you both wrote, I think that doing chesed may be different for different people. In one of Rebbetzin Heller's past shiurim, she mentioned that we are only required to give what we can. I think part of it is learning what each one of our strengths are and trying to actualize those strengths to help others. It may not be going out into the community for everyone, for some it could be doing chesed for their family, or helping their neighbour in a difficult situation. I don't think that we can expect the same type of chesed from everyone. But I think that we all have to strive to do our part and then Hashem will help us feel that pleasure.
As Rebbetzin Heller expressed, doing good things results in spiritual pleasure. If we really sensed the spiritual delight in doing good things, the quality of our kindnesses would be much greater. Our pleasure in doing Chesed would be so apparent that the recipient would not feel guilty or indebted to our deed. Our attitude shift would also include a desire to pursue opportunities rather than wait for opportunities to present themselves.
Hadassa, you mentioned that "if we really sensed the spiritual delight in doing good things, the quality of our kindnesses would be much greater." I have always had difficulty w/ doing Chessed b/c it s not something which comes as a natural trait. I don't have the nature to go out into the community looking to do Chessed. Therefore, I wonder if someone has an inherent trait to do Chessed or any other middah, will the quality of their kindness be greater and be felt more by themselves?