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As for the legality with the FAA, why would you care?
That's his problem if he breaks a regulation.
FAR Section 61.113(c)
– Private pilot can share operating expenses with passengers provided the private pilot does not pay less than the pro rata share of the operating expenses
– Limited to fuel, oil, airport expenditures, and rental fees
– Purpose of flight must be bona fide joint venture for a common purpose
I bet an agent from FAA legal could make the argument that providing the air transportation is an inducement to buy his car. Also, if he turned out to be a car dealer, then the flight is no longer incidental to his business... it is in furtherance of his business.
Now, if he breaks the plane... then it's your problem.
What are his insurance coverage limits for you if there is an incident? Many privately operated planes only have about $50k of passenger medical coverage.
Not saying you should not do it. Just stuff to think about.
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The souls of the righteous are in the hand of God, and no torment will ever touch them.
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