A quick thought that came to me as I woke up this morning:
Do we gauge the value of tzedakah based on what the recipient gets, or based on what the donor provides?
From a utilitarian ["Did the indigent receive help"] perspective, we would look at the benefit to the recipient – if I give him something he can’t use, there’s no mitzvah. If someone is starving and I give him a roll of gift wrap, I have not fulfilled my obligation. After all, the biblical mandate of די מחסורו, “Give whatever he lacks,” dictates that I base my gift on his needs.
On the other hand, from a mitzvah ["Did you fulfill your obligation"] perspective we do calculate based on what I give. Case: If I give an indigent person a ride to his relatives for Yom Tov, and it’s a 200 mile trip so that I saved him a great deal of money, that’s a tzedakah contribution. However, if I was going in that direction anyway then I can’t count that toward my maaser kesafim, my 10% tithe, because I didn’t actually give away anything.
Perhaps it’s a difference between the mitzvah of tzedakah and the practice of maaser kesafim, of tithing my income. For tzedakah purposes, we gauge by the recipient. For maaser, we gauge based on what I gave?
I think there’s a lot more to say here, but it’s time to go. Perhaps I'll add more later.