[tevake]

One way to have an easy time selling a car is to price it to sell. First decide what you think it should go for in the retail market. Then determine what a dealer will give you for trade in.
Then split the difference, probably quite a bit of difference. You will arrive at a price that should move the car quickly. And still yield quite a bit more than the trade in.
As to the tax picture, well Eric could well help you with a situation that deals well with the tax issues, And most likely help you into a nicer car than you would be able find locally.
Quite a few here at PP BBS have worked with him and shared the happy outcome with us on the forum. It may be worth looking into.

Good luck with finding the right new car, and deal.

Cheers Richard