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.
I have a lot of experience working with specialty insurance brokers who can build custom policies if necessary depending on what you are trying to build (eg, new carshare, rideshare services).
If it is a traditional car rental program, you'll need to find a broker who provides that type of insurance. You could try asking local rental companies who they work with and ask for a referral. Having a small fleet and working with low income populations (eg, possibly no credit cards) adds some risk and challenge for getting set up. You said "some" of your cars will be leased. What about the others? The first question you need to answer is 'who owns the cars'. If you are trying to do something peer-to-peer, it will add cost and complexity and there are fewer options for who you can work with. I'd suggest doing one or the other and avoid mixing the two.
Happy to discuss in more detail on a call.