How much do you think this dent will cost to repair?

honestly, i would say about $1,200- 1,500 since its dented and needs paint. That means the dent guys charge for the service and labor and then the paint guys for materials, labor, and usually an hourly rate on top of that. Tell him to get as many quotes as possible. He has the right to pick the repair shop but if you tell him that you want to pay out of pocket, he may understand and work with you on getting a lower price