This is the type of thing that is a definite time sink for P&C agents. When you have someone with a bad driving record, carriers don't like high value cars. They pretty much figure they are going to write the check for the car and so why bother.
The thing you may be able to do is see if you can exclude the high-risk driver. May not be an option though, especially if that happens to be the owner of the cars.
I like a few of these challenges from time to time, but I usually regret taking them on when I add up the time I spend trying to find the solution to the problem.
Dan
