We give a little bit to those who ask, we don’t check to their stories, and cut conversation short, lest we induce them to lie. If they don’t really need the money, BH. But you are suggesting we give 20-30$ every day to anyone who asks? Did you give out money like that, when you were well-off? If so, how many times were you taken advantage of?
Most people will gladly write checks when someone we trust talks to us. Let me tell you an interesting fact of life: only a small fraction of those who truly need and deserve help, will ask for it. Lots of people will do the impossible, beg for work everywhere and cut every expense, even essential ones, but do not ask, and if ever they receive any help it’s because some kind soul, usually by chance, stumbles upon their predicament and becomes aware. If you feel insulted by two dollars, to the point you basically curse those who open their wallet (likely for the umpteenth time in the day), I am very sorry, but I can not help it. One last thing: I happen to see people who are in desperate need themselves and yet open their wallet and give a dollar to a fellow jew.