I am thinking about starting a rental car company in my area a region that is fairly underserved. My fleet will be very small (i.e. less than 5 cars) and the people renting them will, for the most part, not be very wealthy. As a side note some of the cars we may rent out will be leased or financed from a regional dealer.
I am regularly asked questions similar to this by new business owners or business owners expanding to a new venture. Insurance has many niches that exist in the commercial insurance space, this is one of them. A couple of places to start;
1. If you already have a broker who handles commercial insurance this would be your first conversation.
2. Even if you have that, a second opinion is a good place to start. Do a quick search in an area in a different part of your state. Try and find a similar operation. Call and introduce yourself and see who they use. Since you are not competition they are likeley to gladly make a referral.
3.Typically associations have a ready made policy just for you. Give this a shot; https://www.acraorg.com/
4. if leasing from a larger operation, I bet they have someone ready and willing to speak with you as well.
Best of luck. Happy to chat further.