Roberts will have to go further than a tropical island after he pulls this disaster off...The moon perhaps?
He likes to go to Malta on his vacations. He purports to be a devout Catholic, but I would not be surprised if he is a member of some secret society. I think he might have some relationship with the Knights of St. John (Hospitalers)
0bamacare is designed to destroy the middle class and Roberts is called to be a major actor. The penalties begin as one enters middle class income, so there are substantial incentives to keep your salary low, get the government benefits, EITC, Medicaid and do side jobs for extra cash.