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With regards to insurance - and I speak from experience - NJ registered truck involved in an accident in South Dakota.
Insurance company says it's ok for the guy to be paying me to move his boat from NJ to Washington State as long as he is riding with me, they say that's permissible under the ride sharing and carpooling provisions of the standard vehicle insurance.
If he is not riding with me and is just paying me then they consider it hauling for hire and therefore a business and need commercial insurance.
So you can do your friend or neighbor a favor and get paid for it, they just have to be with you.
Be careful with your load and work with people that you like. You gotta start somewhere if you're wanting to do some hauling, and there are too many costs to just jump into commercial without already having a network.
There honestly and harshly is No way to be a "truck for hire" business guy, without having every single part of what is needed by law. These things include, commercial registration, commercial plates, commercial liability insurance, commercial cargo insurance, third party trailer insurance (if you plan on towing other people's trailers) and in the states, you'll most certainly need DOT Numbers, MC numbers, a licensed and registered company name and logo on the truck, use all DOT approved cargo tie downs etc. This video I made back when I was the owner/operator of my own commercial light duty hotshot & transport business may help, others have gotten much help from it in the past and I hope you do as well. If you operate illegally without all this stuff I listed, the fines are very steep if you get caught, and you seriously risk getting sued by clients if you get in an accident and or damage the clients property/cargo item without the proper insurances. It is a recipe for incredible amounts of disaster to say the least. But anyways, here is the video link I made a year or so back. I really hope it helps you and others who desire to enter this field as a commercial, owner & operator ie. a truck & trailer for hire sort of business.
Rezvani's Latest Post-Apocalyptic Monster Is a Ford F-150 Raptor Underneath
Slideshow: Called the Fortress, the 850-horsepower pickup combines Raptor underpinnings with military-inspired features, survival equipment, and a starting price of $285,000.