The coin doesn't get re-rolled. Our armored courier picks it up in a bin and then takes the bin to the FRB. Since this is our practice...it will always be new coin he is seeing.
I don't understand it either. Looking for silver quarters would be more lucrative. But we usually do whatever our customers want...
Silver quarters are getting more and more difficult to find as more people are looking for them. As a person who goes through a roll+ per week on laundry, I can say that I've gotten 2 silvers in the last 6 months!
He obviously has an abundance of time, and every wheat penny is worth about $.025, and can be sold by the pound to many coin shops, and those are still relatively common to find in a roll. As far as fees, I would start by simply having a conversation with this specific person. Inform him that it is a strain to accomodate the volume he is requesting, and that you have fees associated both with getting the rolls of coin, and returning the loose change. Many people seem to believe that $$ is just traded around and don't consider that every time you're selling them a roll of coin, you're likely losing money on it.
I'd bet he's tried this elsewhere and had fees associated, just like a business paying a fee for a cash order. Unless he's told that this is a problem and may result in a portion of the transportation fees being passed on, he will surely keep doing it. Otherwise, by continuing to make concessions and express no issue with this behavior, you're just enforcing it.