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1. Am I allowed to purchase a firearm for the sole purpose of reselling it to a private party, face-to-face?
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No. That is a straw purchase. At the time of the purchase, you knew you were not buying the gun for yourself (or to gift).
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2. If so, at what point is the sale no longer a straw sale? What criteria must be met?
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Your
intent is the deciding factor. You could buy a gun from a FFL at a gun show planning to take it home and add it to your collection. Half way around the room, you could bump into someone that offers to swap you for another gun plus give you $100. That would be perfectly legal. You did not lie on the 4473 because at the time you filled it out, you were truly buying the gun for yourself.