ok.. lets' do some math.. let's say he has 4 homes worth 8 mil each that's about 30k.. with expenses and hoa's and whatnot, figure 35k per, so that's $140k/month just in mortgages (anybody with a financial advisor would NOT be buying these homes outright, and they'd surely carry a mortgage)... then he has the cars.. I have no clue how many or what he paid.. figure a just a flying spur will put you down $3k/month if you finance it.. figure he's paying at least 10x that amount, so $30k in cars.. then there's the watches, which just going by the pic look like basic cartier ballon's and whatnot...looks like an omega, and a Daytona, ect.. assume those are platinum or white gold so that's about 30k/watch, then add in the 'custom' crap (diamonds).. and those run up to about $100k (of which he'll NEVER resell it for.. a $100k Patek or IWC will easily resell for $100k+ without all the buffoonery bling on it.), figure he has about a dozen of those, who knows if they're financed, I doubt it.. same with the diamond encrusted chains.. so figure he's got about $3 in jewelry (being conservative)... oh, don't forget the maintence on those lambo's, Ferrari's, bugati's, rolls and Bentleys, that's running about 10k/year each, maybe he gets a bulk discount.. so figure he's spending $50k at least just in maintence each year, depends on how much they're driven... then they's the yacht with besides the pricetag (which comes with horrible depreciation/resale), figure that's financed as well, and figure he paid about 20mil for it, with insurance figure he's paying mayne 60k/month, and operating expenses with yacht's is a fucking dry anal rape when you figure with something that size, you're probably getting 60 gallons per hour at 15knots cruise (could be worse, could be better, I dunno what kind of yacht he has or what kind of motors ect..) plus paying for a crew to work on it, taking it out for a weekend will put him back $15k easily.
ugh... then you have his groupies and hangers-on. I don't have a clue how many or what they're paid for whatever they do... figure he has 100k/month just on them (which is probably a conservative estimate).. that's 1.2mil a year.
oh... so let's add some of this stuff up...
mortgages = $140k
yacht = $75k (assuming he takes it out one weekend a month)
cars = $35k (including maintence annualized)
yes-men & employees = $100k
so, not counting the gambling or jewelry or other living expenses (alimony or child support or legal fees from when he beats up another woman), that's just about $350k per month, or $4.2mil per year.
so each $30mil payday gives him 7 years (probably more like 5) of living expenses.
now, he has what 500mil in earnings? pre or post tax? I dunno...
lets assume he has 100mil invested, in an easy and safe 'fund' or fund(s), that put out 5%/yr.. that's $5mil per year pretax, more than enough for him to live comfortably on, even if he's spending it like a fool..... especially since he probably has more like $200mil invested and returns average 5%.