D was surprised this hasn't happened sooner but I had my first contact with an unreasonable potential buyer for some of my stuff.
He not only gave me the sob story of him being a single dad etc. and he wanted to give this item to his daughter... The old softy me, having marked down this otherwise new item down by 50%, proceeded to reduce it by another 40% so he could afford it.
Then the bickering started. We are talking less than $4 here folks. He wanted the shipping billed to the penny and wanted to disregard my cost of packaging and doing business ie. the paypal fees, the packaging fees and the gas, time and effort to get to the post office so that he could buy this item at a bargain because I felt for his cause.
After his 3rd email, I decided not to do business with him. He had the gall to write back to ask me to contact him if I changed my mind.
I'd rather donate the item than sell it to him. To me, it seemed like he was being hugely ungrateful. I certainly do not need the money as much as he apparently does.
If less than $4 is enough to put him over the edge, then maybe he is trying to wear a hat that is too big for his head. He ought to consider an item/label that is within his comfort range so that he wouldn't have to go to such embarrassing lengths to make ends meet.
Personally, I would not be inclined to put myself out there like that to try and gain sympathy so that I can buy something I cannot afford. I also wouldn't expect someone to make a special case for me. Perhaps I wasn't really doing him a favour by being generous.