The thing about Hilary Clinton is that she seems to always take the side of the correct, while managing to be to as candid as possible with the usual dash of charisma, not to mention caution. Briefly, she is complex. While I think that it makes for a very well-rounded person, I think such a fine balancing act that she has to put on all the time makes her too complex to win an election.
Drew Westen has written this very interesting book called "Political Brain: The role of emotion in deciding the fate of the nation" & it has some remarkable insights into the human decision-making model. Apparently, & rather sensibly (with the advantage of hindsight), it appears that evolutionarily the rational part of the brain developed way later than emotional part & Westen theorizes based on ample experimental data that our decision-making continues to be largely an emotional activity & rationality has little part to play in it.
This is precisely why economists like Manmohan Singh may fail at popular elections & folks like Narendra Modi & Lalu Yadav continue to be champions of the political game. Well, my intention is to not bracket Modi & Yadav in the same bracket because that's how I see them as politicians, but more because they have an element of identity with the masses (at least a good majority) & connect with them at levels beyond the intellectual.
Clinton would do well to do less balancing. Because the votes she is going to get out of folks who will value her for that kind of a thing are not nearly going to be enough.