The article below is pretty in-depth and technical, but gives a great insight into the housing bubble. We of course know now the housing market was a bubble, and that many parties had a great interest in keeping that bubble going. What this article talks about are the people who made money when the bubble burst, and their role in making sure the bubble got as big as it could possibly get. It talks about how funds used Credit Default Swaps, a form of insurance against a housing default, as a way to bet against the housing market. This would be akin to seeing that a hurricane was making it's way to land, and buying run down houses on the shoreline, getting them appraised for 5 times their value, and then buying hurricane insurance against the same properties.
This one is long but eye opening stuff..
The Magnetar Trade: How one hedge fund helped keep the housing bubble going.