You would both need to be on the policy since he will be driving the car and you will own it. If you will not be driving the car, he can get the policy in his name but you will need to be listed as an excluded driver, which means you are not covered to drive the car.
Car insurance is incredibly specific - it can change based on your zip code and the VIN of your vehicle. So, it's going to be near impossible for me to give the company or car that will be the cheapest.
The maximum allowable number of drivers and vehicles that can be insured on any particular car insurance policy will vary by company. While there is no set standard, most insurance companies will allow their customers to insure up to 4 drivers and 4 vehicles on a single policy. This does not mean that you cannot insure more drivers and/or vehicles with your car insurance company if that becomes necessary.
A car accident can have a fairly significant impact on your rates so if they damage is not extensive, as you say, you might want to consider paying for the damage out of pocket. Ultimately, that decision is up to you, but our State of Insurance Report (page 58) shows that at fault accidents in North Carolina will cause an average rate increase of $426 per year to your policy.