About 5 years ago, I sold a truck that I still owed money on. It's awkward not being able to give the new buyer the title right away, but if you're willing to do a lot of extra legwork, and to sell the truck for a little bit less, it can be done. I had the title in the new owner's hands in a matter of weeks. Of course, you'll still owe some money for a while, but it's better then any of the alternatives.

BTW, being car-free, it's way more fun not having to deal with stuff like that any more... as long as I live in a big city, which is highly likely, given my job, I will never, ever own a car again. It's just lot easier not to have to bother with that nightmare.