Avik Roy has good rundown of the Obamacare disaster as it was unfolding, almost from the get-go. It was always going to be too complex an operation to work, but the project was made that much more difficult by the fact that it was almost entirely a political operation. The sheer incompetence is mind boggling, but the arrogance of these supposedly all-knowing collectivists has, unfortunately, become all too familiar.
Hmm. It's as if they are so conceited about their abilities to micromanage society that it becomes fatal. Now where have I seen that before?
Update: Glenn Reynolds recommends a book that offers some lessons for those with grand schemes to perfect society.