As an experienced Independent Insurance Agent I consult individuals and business' on their retirement, health and life insurance needs.
I'm a Licensed Life and Health agent in NY state, my areas of expertise are in personal and commercial insurance consultations.
Basic Errors and Omissions insurance should cover what your describing. There could be local/state laws concerning running the vehicle for prolonged periods of time, a call to your state department of permits should give you a solid answer to that.