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The nice thing about multiple people going in is you can tagteam them into a better deal rather than get steered into a certain line of conversation. They like to throw stuff at you like how much of a monthly payment are you looking at. Don't fall into that trap. Just go right to the numbers. The more upfront you are with him the better to keep focus on the price and more importantly the lowest price possible.
I assume you're going to avoid mentioning what site everybody's from in case he goes fishing for details?
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