If you're going to haul for-hire, you'll need at least $500,000 worth of commercial liability insurance, a DOT number, interstate operating authority (if you leave VA), depending on your weight, a class A or B CDL, and oh yes, you'll also have to participate in a random drug screen pool as well.
The easiest way to accomplish most of the above is to lease yourself and your truck to a commercial carrier, who takes a cut of everything you do (usually 20-30%) For this they provide the commercial insurance (legally, it has to be in the carriers' name, not yours) carry your receivables (do your billing) arrange the drug screen pool, track your mileage for road tax and audit your log books (oh yes, you'll need a log book too)
You can get your own authority for around $1000, plus you'll probably be required to front a 25% deposit to get your insurance policy started (you should expect to pay about $3-500/month for this policy) you'll have to bill and collect all receivables (some people/companies will run you out to 120days) file all road/property taxes (yes, you'll be paying property tax to states you don't live in, because in their eyes, if you drive through, your conducting business in their state, and your truck is business property, which is charged tax based on it's value and the number of miles you ran in their communist state...BTW, KY is the #1 communist in your area). On the up side, you should be exempt from IFTA fuel taxes.
There are very few insurance companies writing commercial policies, and even fewer still writing them on pickups. Progressive used to write commercial policies provided you do not go beyond a 300mi radius from your home terminal (base of operation), I don't know if they still do. Northland Ins. will write a policy on a pickup without restriction, Marvin, Johnson & Associates is a big commercial broker, and they are Northland agents.
There are a lot of "bootleggers" out there, running illegal in pickups. With no insurance, authority, CDL, drug screen, etc. They haul for cheap and make it nearly impossible for someone wanting to run legal to make money. I would not advise this avenue, as when (not if) your are either caught by DOT or involved in an accident you will be hung at the nearest convenient tree if not by the DOT then certainly by the "victims" lawyer (I quoted "victim" because you WILL be at fault reqardless of the circumstances of the accident, do to the fact that you are illegally operating and shouldn't have been there to begin with)
Sorry to ramble, but after 20+ yrs of commercial hauling, I just wanted to you to know what your getting yourself into. /ubbthreads/images/graemlins/phoney.gif
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I dont think you would need any type of insurance for something that small of a hauling operation.
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The size of the operation has absolutely nothing to due with the legal requirements, if he's getting paid to haul goods he's commercial, and must comply with all DOT regulations.