1. The job market, especially in media jobs, has changed into one where you can be fired at any time. Similarly, forty years ago, someone who had a good media job would not have felt safe making such inflammatory (right or wrong) statements.
2. American housing markets have adjusted higher to essentially consume all of the practical discretionary income of renters and buyers. A lot of this has to do with the securitization of these obligations, and the corresponding loosening of credit requirements. If the rope that the bank or the landlord is willing to give you increase, it's not just a personal decision about how much risk you're willing to take, because it affects the loans and leases everyone else in the market gets. Just because your neighbor is taking out a crazy loan he can't afford if anything goes wrong doesn't mean he isn't pushing up the housing prices just as much as if he could do it comfortably.
3. The financial markets have become much more sophisticated on one hand, but also much less local and much shorter term focused. If 10% of borrowers default, that's not necessarily a problem as long as the cost they cause covers the profit from the others. If the 10% cause major social problems, the holder of the CDO in Qatar has no idea, and wouldn't care if he did.
4. The increased availability of credit, and the increased willingness of markets to give credit to risky borrowers has forced people to extend themselves to the max in order to compete for social status. If your friend has a BMW and a big house even though he's practically bankrupt, you are pushed into doing the same thing. The girls at the next table at the bar have no idea that he's is being fiscally irresponsible, they just know that he has a cool car and a nice house.