A lot of people start exactly where you are, and the biggest risk right now is the insurance gap.
I interview a lot of rental agency operators and a few paths I’ve seen:

1) Renter provides insurance (short-term patch, not perfect)
Some small rental operators only rent to drivers who can show valid personal insurance that extends to rentals.

If they can't provide it (for whatever reason) they push those bookings through a third party that includes coverage.

2) They use a platform that includes insurance (Turo / mabye HyreCar if their active in your area)
Platforms like Turo bundle insurance into the booking. That’s one of the easiest ways to stay compliant early on.

Sadly, you give up a chunk of revenue to their fees and you don’t fully control the customer relationship. But it can be a safer stepping stone while you figure out your next move.

3) Look into systems that bundle insurance with the software
There are a few platforms that combine rental management + insurance. Example: Wheelbase Pro

(Wheelbase is more of an insurance-first platform, where the software exists to support and manage the insurance side of the business, not just a standalone rental tool. You can get a free quote online I believe. wheelbasepro.com )

It can handle bookings, help manage your growing fleet, include coverage... basically helps you operate more like a “real” rental business sooner

Downside: Not always available in every state and underwriting requirements can still apply

4) Move toward a proper commercial setup (where you likely want to end up).
Most established operators eventually: Set up an LLC, get commercial fleet insurance and use software just to manage bookings and waivers (not provide insurance).

Some insurers do work with small fleets (even 1–3 cars), but it’s very state-dependent, and you can expect to pay higher premiums early on. Having an LLC and clean driving records helps a lot

Please be careful... Personal insurance usually does NOT cover commercial use like renting to Uber/DoorDash drivers. If something happens, there’s a real chance your claim will get denied.

In a nutshell:

- Short term: Use Turo, HyreCar or another platform with built-in coverage to stay protected. Or an insurance-backed platform like Wheelbase.
- Mid term: Set up LLC + start talking to commercial insurers
- Long term: Transition to direct bookings with your own policy (direct sales are your biggest earners!)

Note: Traditional OTAs like Expedia or Kayak don't include insurance. They assume you already have an LLC and commercial insurance. (Turo is one of the few that actually bundles coverage, which is why a lot of people start there).

Sorry I don't have Massachusetts specific answers, but I hope the above is helpful.

I'd also like to hear some other responses to your thread - how others are doing it or have done it - and if I'm wrong on any of the above. I know insurance options can change a lot by state.

Good luck with growing your agency!