A couple of observations:
Do all bankrupts drive around in Audi Q7's? If so, I might consider that route.
Regarding his "investments", if he was so badly advised, why doesn't he sue his advisors? I think this is just a smokescreen. He probably put 5-10% down to buy the properties, borrowed the rest then couldn't make the mortgage repayments as his income dried up. I'd be surprised if he made much of an effort to repay any of the capital outstanding.
I wish the man no ill-will - I wasn't a huge fan (IMO his England cap marked the pinnacle of his career) - but I'd be amazed if he hasn't just pissed the vast majority of his wealth away.