Dear Khalil Bodhi,
I guess the article The Lessons of Gratitude
is good to understand the generosity and kindness we need for a wealth society and the aspects of Dana which are actually beyond this.
While for example Asian people tend to provide a health but also incredible bounded relationship network incl. also the Sangha (incredible caught in the misunderstanding of demand and dept, forgetting the way out), where all is a matter of giving and taking, western people tend to settle their obligation outside of the daily community (which is often a runaway when responsibilities according to what we take are not taken).
Actual the second is more in line of what make a society more free if it is done rightly, but it can also produce additional bounds which may be additional irritations. We need to be very careful that our Dana is really Dana (letting go without any hope of a reward).
That is also the reason why people having lot of understanding in Dhamma a seriously practicing it, do not have a easy life when the surrounding does not follow or understand the ways of letting go but requesting a direct equivalent of what they see as an scarify.
I guess the most secure and best way is, to induct those around one self as best as possible and make Dana to an collaborative action. Otherwise there will be conflicts and bad conscience as well. It is not an easy way to teach others that generosity has only positive effects if it is an expanding spiral and we can easily build up additional demands and dept.
That is why I told it is not easy to find the middle or a health way for all. Dana in a worldly manner gives us worldly secure. Dana in a real letting go manner, as a tool to step deeper into Dhamma beyond the mundane live gives real security.
I guess if it becomes more and more to a question between those both its good to turn on the Sila screw, than we do not have to think to much about our Dana work any more.
It's not only difficult to give without wishing something back, but the point comes that it is also difficult to give not back in the way people would usually expect. Than it is the question: "Can I get through it, am I honest in the way I do?" Actually it's a natural Dhamma force to climb up the next stages.
Here the sutta which Path was maybe referring to comes into play: Velāma Sutta: About Velāma
(Even highest dana is "only" one of 10 wholesome deeds; also here one can see that Dana was a family-head thing and not that much a personal thing, as we are used today; if we are not the head we can do our best for our head. For sure it's not easy today. *smile*)
The more one becomes to somebody in Dhamma, the more he will provide a possibility for Dana for others which gives additional push we might "misuse" also in the direction back.