Though Obamacare has been the law of the land for 3½ years, this marks its first major milestone that impacts Americans on an individual level. That's because Obama designed his crowning achievement to phase in slowly, over nine years—probably a good idea considering it's a hive of onerous regulations and 20-something new taxes that, if unleashed all at once, would wallop the US economy. Better to boil the frogs slowly.

The next major milestone is approaching fast. On January 1, the individual mandate will take effect, forcing all Americans to either buy health insurance or pay a penalty. Well, almost all Americans. If you happen to be friends with Obama, or a donor, union, or political ally who supports him, you may get a waiver, which you'll read more about below.