Mission, Franklin and Lamar. Objective, deliver repo car with minimal damage. I have driven so carefully as to not touch anything, three times over. The objective is greyed out in the replay screen, and I know I've achieved it at least twice. Do crashes accumulate through retries, or what's going wrong here? Mission, complications. Objectives, complete in 5:00. I timed myself doing it in 4 minutes 37 seconds, once again, objective is greyed out in replay screen. What am I doing wrong here?
Damage to the cars should not prevent you from unlocking the gold medal via retries. It is possible you are damaging your car unintentionally. Hard landings will damage the bumper of the car and are difficult to avoid when driving over some of the bridges on the mission route. It is also possible that you encountered a glitch while playing the game.
In short there isn't really any other qualifiers to complete the challenge for this mission. The repossessed car was either damaged during the drive or your game is bugged.