Each policy would be separate. They would take out a different payment for each policy.
Car Insurance Costs
The decision to maintain your auto insurance coverage is really dependent on whether or not you plan to buy a new vehicle in the near future. If you cancel your policy and then buy another vehicle within the next month or two, the insurance rates for that vehicle will be much higher than if you maintained coverage.
Coverage & Claims
The decision to file a claim would be completely up to you, but in Massachusetts, an accident has an average impact of more than $700 per year in additional premium. If the repairs are less than that then I would recommend paying for the damage out of your own pocket.