I don't think Obama being an outsider hurts as a vp. In the "change vs experience" argument it really is revolving around the top job.
I am not convinced Hillary would offer (or that Obama would accept) though.
There is a history of contentious elections resulting in "that would never happen" running mates though.
I can't see Edwards wanting (or being asked) to be VP again, especially since he didn't "help" Kerry in the south last time.
Whether it helps or not in reality, they will pick the person as though it does.
I think the best bet for a Hillary VP is Wesley Clark or Richardson. For Obama, again Richardson is a possible one, but I think he will pull in someone "with foreign policy creditials" that I can't think of now.
I stand corrected, you are as vapid as they say.