I'm sorry, but there is no sane "compliance" department that would ever let a transaction like this happen. It screams of conflict, looks shady regardless of whether or not it actually is, and is just administratively burdensome.
Why would you even want to bother with the amount of paper work required to justify this transaction when you can find the same car 15 times in the Sunday paper.
Even if this is "legit" in the eyes of the NCAA, it's a horrible practice and speaks volumes to uk's idea of compliance.