I don't view this guy's problems as a lack of formal education, but rather very poor business judgment, which tends to be liberally distributed across the spectrum of educational attainment.
Smart people make dumb decisions. Dumb people make smart decisions.
I do rememeber the marshal reddick seminars. If I recall, reddick teaches at SDSU (or is affliated). I recall he was the empitome of overextending. I know a lot of people who followed him. I hope they are ok.
$9800/month negative is crazy. As far as bankruptcy rules. Latest bankruptcy rules don't allow you to completely wipe out debt.