Daniel Reeves (co-founder of Beeminder) blogged about how collision insurance is a ripoff (8 years ago, but I just found it today). He got some pushback and didn’t have the exact math to win the argument. As a professional gambler who also reads a lot of company financials I can provide the exact math for when the average driver should buy collision insurance.
I think your edge from having knowledge of the drivers on the policy can outweight the house edge, speaking as someone who's "won" that bet :)
Ha! Beautiful! I'm finally vindicated :)