I used to work with a guy who was in his 50's and he'd pull that stunt.   He'd be underwater on a pickup and he's just trade and roll the old debt into the new vehicle.   This guy wasn't a farmer, he was a postmaster and didn't need high priced pickup.   The rest of us at work couldn't believe any dealership even found a finance company that would go along with this, but he always did.

Sad thing was he actually thought he was doing the right thing by rolling the debt over.   He kept talking about all the equity he gained by trading for a higher priced vehicle.