Suz, I think it's less that I'm not sure the charity items found a good home than that I don't know what home they find. I'm more likely to think, "I want that denim skirt back!" if its destiny is mysterious.
I gave my niece an almost-new BCBG leather jacket in a beautiful, unusual shade of leaf green because I had to face the fact that the shoulders were uncomfortably snug on me. I LOVED that jacket, but the next size up was too big and the one I got was just too tight in the shoulder area.
Anyway, I hemmed and hawed before passing it along to Dainty Shoulders Niece but finally did, and I have not regretted it for one second. She wears it constantly and the cut and color suit her exquisitely.
If I had sent it to the donation pile, I would probably still be second-guessing that decision and wishing for it back, promising the wardrobe gods that I would wear it, really I would, I just would only wear it with a light tee beneath so it didn't feel SO DARN TIGHT...