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Why don't you set up an LLC, and in the event that he sues you, he gets the company truck or something else that you can financially absorb fairly easy?
Then write up a contract between the LLC and him that joins his obligation to the LLC with a self-employed status. No taxes, no workers comp insurance to deal with, just a mere 1099 at years end.
You may not be able to do that where you are though.
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83 944
91 FJ80
84 Ram Charger (now gone)
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