Radley Balko basically captures all my quibbles with Obama in his latest Fox News column (yes, he does a column for Fox. Get over it.)
The thing is, every single one of these are politically easy positions. Willie Nelson has earned my everlasting ire (despite his absolutely amazing collabo with Snoop Dogg [SPOILER: IT'S ABOUT SMOKING POT]) for his free memetic PR on behalf of the Farm Lobby; similarly, nobody who is interested in getting elected to anything and is not either a certain crazy elf from the Midwest or a certain web-popular Texan Obstetrician dare oppose the War on Drugs or expanding federal powers. Needless to say, a Democrat who goes against the Teachers' Union has all the chance of a Republican who hates Jesus.
It's not surprising, it's just a good reminder to certain people (like my father) that simply electing a youthful, charismatic, less-evil-than-most-other-politicians Black guy is going to magically change the world.