I just watched this video from the Obama website entitled, "Meet Barack." It details Obama's family background and political rise. I think the Obama campaign seriously needs to consider creating a distilled version of this ad to air in Pennsylvania and elsewhere. I believe they're going to need something like this to counter the GOP slime machine in the GE, anyway.
Most voters probably wouldn't see Hillary as a stronger candidate on issues such as health care and foreign policy if they didn't have doubts about Obama's experience and background. Simply repeating his policy stance is not enough; he needs to show people where he's coming from. He has one ad that does provide a little bit of info about his younger days but not enough about his family background.
Most voters who have doubts about Obama's religion and "mysterious" background would benefit from seeing that, while unique, he's not as "exotic" as they're being led to believe; after all, as the video points out, he was raised by his white Kansan grandparents. This does a lot to dispel the myth that he was raised a Muslim. Does Obama need to prove his "whiteness"? No. But it wouldn't hurt to show voters who he really is and help allay their fears, no matter how irrational or unfounded they may be.