Logician, with all due respect that is really blowing up and twisting things a bit.
I actually was thinking as I read this and heard that you require $1000 from someone who doesn’t have it for doing chessed, that makes me wonder why I would want to be part of the yeshivish community at all! If Hashem is happy with a “gift”, how dare you act like $100 is an insult! You have turned this Holy work into a business and are upset that your attitude is turning stomaches. It isn’t halacha we are arguing with, Ch”V, it is your somewhat skewed interpretation of it.