answer:Interesting question. My first reaction is that if you can’t afford to just do it, then don’t. Obviously, the people you knew could afford to give that away, of they wouldn’t have. What’s interesting is if you switch the question around a bit and ask “Should you be able to designate the recipient of your charitable contributions, as long as that person is already clearly qualified?” On the face, I’d say “Yeah, why not?” After thinking about it for about 5 seconds I know there’s no way to prevent people from abusing that. It would be nice if there was a way you could give your car to a truly needy friend or neighbor and get the deduction. It would be incentive to charity with the deduction helping offset the loss you’d take not trading in.