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Sometimes it works. For example I just traded our 2012 Tahoe on a ML350 for my wife.
I listed the Tahoe in our local Autotrader. A wholesaler contacted me right away and offered X amount for it. That number was higher by $2500K that what the dealer offered for trade in value.
When I went to purchase the new vehicle I told them I would handle my trade on my own and had an offer much higher than the one they provided. They came back to the table with something about $1000 less, which in turn was really the same because of the tax savings of doing everything in one transaction and the same place.
I did the same thing when I purchased my X5 and it worked almost exactly the same way.
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