Getting a new car with an upside-down loan?

I was writing to possibly get a consult on a dilemma i have. I recently bought a 01 ford f150 from a dealership and seem to be upside down on my loan. I owe $7,000 and is only worth around $4,500. I have found a newer truck that i like that books for $14,000 but is only being sold for $10,000. So instead of waiting to sell my truck out right for the over-bearing price that a dealership asks for, to pay off the lien i have against it, is there a way that i could trade in my current truck for the value to a dealership, and get a loan big enough to pay off the remaining balance of the lien and enough to buy the new truck and put the lien against it? Kind of a complicated question.

Only if the truck you want is at the dealership you use to finance your loan, and I can guarantee it will not be a good deal for you financially in the end. You are not even thinking about the amount of interest you are going to pay over the life of this loan, should you be successful in negotiating such an agreement. Your supposed $4,000 savings would be long gone. You should keep the 01 on the road as long as humanly possible and meanwhile save every penny towards another vehicle. There will always be used trucks for sale.

You could. I would advise against it though… Since you will be even worse off than you are now.

This is what a downpayment is for… When you bought your current truck. You paid a dealer price, not a street price (what you could sell it for), and not the wholesale price the dealer would give you on trade in if you wanted to offload it a day later. Plus the depreciation (which isn't too much for a vehicle that old), plus taxes and fees. Your downpayment should cover at least all of those things… Or you have no business financing.

Your first problem is the $2500 upside down. That has to be paid first.

2nd, there's no way any dealer can make money selling a $14,000 truck for $10,000, its just not happening.

If you can cough up $2500 and sell your old car, THEN you can talk about financing the new truck.

There's no free lunch and everytime you trade cars, you LOSE, not gain, value.