I think you are over thinking this. Step one is to ask what his rock bottom price is. Boom, now you have a new starting point from which to hammer him down. Step two is to pretend to be disappointed and a bit surprised that he didn't come down nearly as much as you thought he should have. He'll see your surprise, then ask what you think is fair, present your low ball offer at this time, meet somewhere in the middle, then enjoy the thousands in savings.
Keep in mind that the buyer has a ton of power. Selling a car sucks. It can feel like nobody wants it and you'll be stuck with it forever. As the buyer, you need to leverage that to get the best deal you can and you can always get it for lower than the seller thought he'd go by using my above approach.
Lastly, for the love of God, don't trade in your car; sell it privately. Trading in is just giving money away. What kind of car are you getting rid of, anyway?
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