My biggest problem with him is that he caves in far too easily to conservatives, giving up ground for virtually nothing, or failing to act in fear of them doing precisely what they'll do anyway.
Good example: immigration reform. The GOP will never, ever get on board with it because a bunch of new brown-skinned people with voting rights is precisely anathema to them, but they pretend like it's an option they'll actually consider, as long as Obama doesn't do anything that actually helps reform happen. And like a sucker, he does nothing. Dude, you're not going to run for another election. Do the shit America wants you to do.
Good example: immigration reform. The GOP will never, ever get on board with it because a bunch of new brown-skinned people with voting rights is precisely anathema to them, but they pretend like it's an option they'll actually consider, as long as Obama doesn't do anything that actually helps reform happen. And like a sucker, he does nothing. Dude, you're not going to run for another election. Do the shit America wants you to do.