Storm,
Although I don't have experience w/ CC, I have had occasion over the years to transport clients for various non-profit/human service, etc agencies. Insurance is always a concern because the agencies consider themselves at some risk should there be an accident involving the client. The question is always whether or not the driver/owner's coverage will hold up in that instance, since transporting others 'for hire' and "when is a passenger not just a 'guest'?" are issues that can be interpreted in many ways.
Assuming that's the nature of your query, I'd suggest you seek out a knowledgeable insurance agent/broker and/or attorney well-versed in motor vehicle tort claims and see how policies written in CT have historically been interpreted in such situations. It's much too complex an issue, has way too many ramifications, and can vary significantly from state-to-state. You can't expect to get a reliable answer to those types of concerns in a setting such as this.
Many years,
Neil
