This seems like a situation where the one would have to be very careful to adhere to the spirit rather than the letter of the challenge. The possible positive outcomes are really great though. I've often been pleasantly surprised (even overwhelmed) at how far people are willing to go to help me, often at great trouble to themselves.
because people think that you really need what you're asking for. By asking without need, you're exploiting the human species community safety net. Only a jerk would reject a request for help, and only a jerk would exploit that situation.