Will a car dealership work with me if I'm gonna lease a new car, while trading in the car I have, which has an outstanding loan against it?

The car I have now has a loan against it which is worth more than the trade in value of the car by about $5000. If me and a family member were BOTH looking to lease a new car (so 2 new cars), does anyone know if a dealership will be working to work with me in any way?

Also the cars looking to be leased are not high end or luxury cars, they d be coming from a dealership like Honda, Toyota, or Subaru.

You aren't going to have a loan to roll it into, so your options are pay the $5K or don't trade in the car

You are "upside down" (have negative equity) of $5000 on your old loan. Dealers can sometimes roll negative equity into a new car loan or lease if the amount is not excessive compared to the amount of the loan or lease on the new car. Typically, they would be able to roll only a maximum of about 10% of the new car value. So, if your new car costs at least $50,000, there's a chance you could roll your negative equity over into a new loan or lease. Whether or not this is possible is completely up to the finance company used by the dealer. A dealer can't make this decision on his own.

Whether you lease one car or two makes no difference here. Trading your old car with negative equity would only apply to one of the new cars.

BTW, when you roll over negative equity into a new car, you instantly become even more "upside down" which is not a good way to keep buying or leasing cars. Negative equity causes problems if you want to trade or sell, but even worse, if you total your car and insurance only pays what the car is worth, not the greater amount that you owe on the loan or lease.

You're going to have to come up with 5 grand in cash to offset your negative equity.

Nope. Unless you both have credit ratings better than 720 and a hefty down payment to make on the new vehicles, that's too much negative equity to work with. If you had the down payment required you would have enough to pay off the loan.

And let's talk about leases for a moment. Sure, if you have sufficient credit and a decent down payment, you can get some great low monthly payment deals - but those only last 6-12 months, and by paying hundreds less per month than a normal car payment you'll soon be in a much worse negative equity situation than you are now. The ONLY valid reason for leasing is if the vehicle is required for a legitimate business where the expense becomes a tax deduction. In the long run, leasing is the most expensive way to drive a new vehicle and it's the biggest financial scam since the mortgage scandal of 10 years ago.

You've already effed up your finances once by choosing a long term payment plan that wasn't enough to keep up with depreciation, and now you're considering doing the same for two more vehicles and you'll be starting out in the hole.to do it. Stop digging while you can or hyouy should get personalized license plates that say Dumbass1 and Dumbass2 on them.

Of course a dealer will work with you. That's how he makes money. He's going to make money out of whatever you do. That's why he's in business.
Whatever deal he comes up with he'll be making money.

They'll just add whatever you still owe on top of the vehicle you're wanting. So you're still paying for both vehicles anyway.

Leasing a car, is a real bad idea. Buying a car, when your upside down on a loan is a really. Really, bad idea, one in which a very short time you will come to regret

They will do anything to get you financed, traust me

Just make sure you bring plenty if Vaseline with you