I was able to help out a friend by donating several 're-gifts' for door prizes at a Christmas cookie party - she was very appreciative. I even wrapped and be-ribboned them beautifully with re-used paper and ribbons.
I donated a 5" TV that we never took out of the box to a local pet store that needed raffle items.
I gave a tea set that had been given to me to a friend to re-gift as her money is extra tight this year and she needed a gift for her sil.
The only boo-boo I've had happen is that when I went to re-gift a coffee carafe at a distant friend's wedding shower, I noticed as I was beginning to wrap it that it smelled of coffee! I washed that sucker with everything I had in the house and it still smelled - and it was too late and I was too broke to do anything differently. I gave it as a gift . It was a good lesson to me to double-check everything that's been 'previously given to be absolutely certain it's in giveable condition...Liz