It's a very logical and extensive argument you have made, but at the end of the day it's human beings that are voting and they have a tendency to stubbornly defy the math. Has it occurred to you that people simply respond to what Obama says because they hear a sincerity that they may find lacking in Hillary? I keep seeing people talking about Obama koolaid, but I don't see it that way at all. He just phrases things in a way I find precise and honest. It may be just calculated political words to you but to me it shows clear thinking that hits all the right points. I hear Hillary and McCain and I hear politics, politics, politics.
It just so happened that Bill Clinton made a campaign stop in my city on his first presidential run. I went to see him on a whim and I was damned impressed, not because he had an abundance of "experience" or was "ready to go on day one" or any bullshit like that. He spoke eloquently clearly, passionately, and I walked away liking the man. I also voted for him.
That's what wins, not all that other horseshit.