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I had a contractor ask me about the use of his cube van. Sometimes he will leave the landlord use it to deliver his goods (rarely). Sometimes he will allow a subcontractor to use the cube van to take supplies to a work site.

I'm wondering what pitfalls there are that I may not have hit upon with him?

The contractor is giving permission for his vehicle to be used in ways that he cannot control after it leaves the premises. There is no legal way he can check their driving record before lending the vehicle out short of asking the driver to provide an MVR each time he gets behind the wheel. He needs to be reminded that he's compromising his insurance and the financial security of his business by offering up the use of his van. Good heart, bad idea.