I just bought a 2007 Mercury Milan for 15,900. it has 18,000 miles on it. The retail is 20,000. It has full Warrenty and GAP insurance. OK so, if I wanted to trade this car in and get a check from the dealership then I can Basically sell the Milan for like 17,000 which is like 2000 more than what i bought it for. Then I want to go and buy a 2000 car and end up paying like 5000 all together for a new car. How does this sound?
New Car 15,000
Loan 25,000
Sell 17,000
+2000 from selling car and can use towards new cheaper car and now i only have to pay off 8,000 of the loan right? is there any other way to go about this smarter. Refinance for a lower loan rate??

First off – did you put any money down on the Milan? What is the payoff on the loan? Beacuase if you got Warranty and gap, you owe wellmore than the $15,900 you paid. Depending on how much you put down, you likely owe for dealer fees and sales tax too. Get the payoff on the loan
Add to that the odds of you getting $18k for it are slim. You didn’t pay $18k. What makes you think you can find someone who will?
If you trade the car in, you will get NO WHERE near the $20k you think its worth. Be prepared to hear m ore like $12K (EDIT – just booked a 2007 Milan Premier AWD. $12,800 is trade value and that is reaching)
I think you need to really re-examine your numbers too. they dont add up at all.