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He won't be labled as being an "inside the beltway" type and that is a very a good thing if you're running for president.
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I think the voter doesn't put much emphasis on years of political service and could end up just hurting you - historical evidence to the contrary v. welcome.
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It seems to me, from a long way away, that voters are keen to elect someone that they trust (ie, can prove experience) but they also dislike the concept of Washington "insiders."
I think this massively hurts Hillary (obvious establishment type) and Obama (very new, young - this is reinforced by his appearance, who strikes me as a very young looking face)
By contrast, McCain, while he has obviously been around for a long time, does seem to generate a "maverick" perception - thus, he has the benefits of experience, but without being tied very closely with the current (or previous) administration.
Australian politics (which I see much more closely) has demonstrated that it is very easy to highlight a candidate's inexperience - see Mark Latham at the last election.
While, obviously, American voters are different people to Australian voters, international comparisons can be useful between culturally similar countries where similar issues are at work.