I want to preface by saying that I am politically ignorant, for the most part - at least for US politics. You wanna talk about provincial and local politics in al Anbar? Give me a call!
That being said, I think Obama would be hanging himself to pick either a female or minority VP. To do so would automatically write him off for a good portion of conservative or fence-riding voters.
I don't know much about the potential VPs he's looking at, save one or two.
I'm not too sure how much Wes Clark would help the ticket. Yes, he's a good leader with a tone of military cred. He was, however, Chmn. of the JCS during the war (and when it kicked off, IIRC?). For all the shit-slinging people do at Petraeus, Clark was in an even better position to affect the prosecution of the War on Terror or in Iraq. That's probably just me, though.
General Jones? Well, he was a so-so Commandant of the Marine Corps, and the first ever to take another post (Supreme Commander, Europe) after his four years in the Corps' top spot. Good guy, but not a *great* guy - although he's been pretty well-groomed for foreign policy, particularly in Europe.
I like Jim Webb, for many, many, many reasons. He resigned as SecNav under Reagan - the
iconic GOP President - over issues of principle. After Jimmy Webb came back from his first Iraq tour (as an enlisted Marine 0311 Rifleman), Jim wore his son's boots every day while campaigning for Senate. And while he was a Marine, Jim Webb won the Navy Cross, Silver Star, and Bronze Star (x 2) in Viet Nam - yet was NOT a career military man.
Dude has shitloads of military cred, as well as DoD and foreign policy insight, but he's not someone who just hung up his stars a year or two ago. He wouldn't have to wash his hands of Iraq because he had nothing to do with shaping policy that drew us there. He's definitely got some skin in that game, though.
Okay, McCain's kid has done a tour in Iraq as well, to be fair. For me, though, the bottom line is that if Obama picks Webb, he gets my vote automatically.
(Although if we vote based strictly on hotness of wives, McCain and the blonde with tits up to her chin win by a landslide!)