Personal coverage from Worker Compensation is reasonable, this covers any issues of working on private property or place of business.
As for transporting goods on your truck or trailer, I can only speak from my Canadian experience.
If my personal vehicle is insured as pleasure it maybe used as transportation a set number of days per month, regular insurance would over going to and from my place of employment but not that of performing duties in commerce - ie any accident arising from this type of work would not be covered. Same coverage as impaired or driving under the influence - nil.
Farm registered and insured trucks and trailers same as commercial with the exception they may burn tax exempt marked fuel same for fishing industry, logging on Crown Lands and Indian Reserves which are classified as private land.
Any truck capable of transporting and registered to carry5500 kg or above is automatically commercial, subject to crossing highway scales and yearly vehicle safety inspections. The chart below may help you with figuring if you need cargo insurance which covers loss and damage to private or public property.
All the goods listed in the chart below are covered by your commercial truck insurance policy.
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