watched 1st 5 mins, IMO, I think he fucked himself up by living way beyond his means , rather by the 08 financial recession.
1. family home from the great great grandpa, seriously ? don't tell me the house was not fully owned.
2. 3 boats , bingo! the guy was living way beyond his means, probably was borrowing $ from the home equity to sustain the lavish live style, common, LOL ( I suspect this guy probably has gambling addiction.)
3. bought half mil house in N. Carolina, let's say this was a bad deal, you got fucked, even the bank gone under, but common, I think it wasn't that hard to play this game, gave the Oakland house to your children, you suck all the cash dry from all your credit cards, turn everything into cash, don't pay mortgage, suck a bit of blood from your own assets, then declare bankruptcy.
Judging from the brief disclosure of his background, IMO, his biggest problem was living way beyond his means, which got himself fucked. Nothing to with real-estate investing.