Wincrasher, IF he can afford the payments on the cars (that I'm guessing are fairly high payments), then he could go to one of those "we finance" lots and buy a much cheaper car with much lower payments in spite of a most likely higher rate. Just because you are upside down on a car loan doesn't mean you keep making payments you can't afford.
This guys problem is debt. We all agree with that I'll bet. All he wants is someone to write down his debt (by the way, look up the tax rules on forgiveness of debt), and he seems to not want to really address the problem of how he got into this mess. In other words, I don't sense he is trying to fix his problem really. He just wants a way out of his current troubles. I'm making a lot of assumptions but they are based on experience.
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