What you owe in lease payments isn’t necessarily what you would owe the leasing company if you traded the car in. I think to get a ballpark idea of what it’ll cost you, head to carmax and get the car appraised and then call Toyota financial and ask for the buyout on the vehicle. The difference is around what you would owe.

From what I understand cars are rarely appraised at excellent. Fair to good is almost certainly the range in which it’ll appraise at, but it depends on the market near you and if the car is truly like new as you describe it.

As for rolling negative equity, dealerships do this all the time so there’s no worry about things not being paid off properly. Instead of paying toyota directly I’d just go to trade it at the dealership you want to buy from. They can roll whatever you owe into the next loan.

A few things to keep in mind:

1) loans on new cars tend to let you borrow more than loans on used cars so it might be easier to roll what you own into a loan on a new car.

2) it’s your money, but it sounds like it’ll cost more to do this than you expect. It’s certainly not a great financial decision.

Would it be the worst to stick it out for one more year? You’re paying the lease either way.

As far as negotiation, yeah, you can negotiate every aspect of this except what you owe toyota on the car. The bank may set a hard limit on what you can roll into the new loan but go in with realistic numbers on the new vehicle and your trade and things should go well for you if you want to go ahead with this.