get the reference number from 311. Then ask them how to start the claim against City of Toronto procedure. If the City recognize their liability, city has its own insurance company to handle this issue. Then you don't need to worry about your deductible.
I hit a construction cone on DVP. My front bumper was damaged. I am doing the claim. Of course, this will take time. But important thing is we could not avoid the accident because of many reasonable factors. Since we are the victims, there should be some compensation. Don't hesitate to use the insurance company, when you need them, they are for you to use. If it is not your fault, your insurance won't be affected. Good luck!