I actually did something like this once. I listed a machine for sale and was contacted by a buyer who was not wanting to drive a 4 or 5 hour round trip, so they arranged for a local car pool/taxi service to drive the machine. All I had to do was drop it off at the taxi driver's house as they paid me via paypal. I think they paid the driver only $5 or $10 as this was a daily route for this taxi. The buyer met the driver at the drop off, carpool spot and saved time and gas $. So, it may take a bit of effort and trust on both parts, but it worked well for me. And I imagine it saved the buyer quite a bit of $.