I have been on both sides of this fence. When I donate now, the item I give is something I wouldn't mind receiving. The clothing I give must be in very good, wearable condition (you would cringe to see some of the "nasty" clothing being given out) and food items must be edible (in date, not opened, and not "weird" [especially no fancy stuff that the majority of people don't eat like snails, oysters, etc. - give good old fashioned peanut better, macaroni, etc.]). Nothing surprises me anymore in what folks will donate...and no, I am NOT slamming anyone here because we all do our best!
When I can, I upcycle my clothes to Goodwill or Salvation Army (usually because I've gotten too fat to fit in them!). I will usually not give folks on the street cash, but I will buy them a hot drink in the winter or a bottle of cold water in the summer. Not much, but appreciated nonetheless. I used to send money to the USO when my son was active duty Marine Corps. Now, I don't do any cash/check charities.
My quilt guild makes quilts for FIT (Families In Transition), QOV and we have a food pantry that we donate non perishable items to, as well.
Thanks to all of you wonderful folks for making a difference in someone's life! You may not know the recipients of your love and kindness, but trust me, it is appreciated!