I voted for Sen. Obama twice, once in the primaries and once in the general election (I cast my vote by mail a month ago.) I am an independent who has voted for Republicans far more than I have for Democrats, but I voted for Obama for conservative reasons. I concede the point that experience counts, but it is not the only consideration. Judgment counts. Temperament counts. Intelligence counts. Intellectual curiosity counts.
As for all the guilt-by-association accusations of Obama, they do not seem very relevant to me because hobnobbing with undesirables is just the way things get done in politics. Obama wanted to be a successful politician in the southside of Chicago, so associating with Wright, Rezko, Ayers, Pfleger, etc. was part and parcel of that desire. What noone has ever demonstrated is how exactly he was influenced by these people. Basically, it seems like he used these people for their local prestige and pull, and then cast them off when no longer useful. While ruthless, this is exactly the kind of thing a President needs to be able to do. Machiavelli would approve.
One key to Obama is that he is an intellectual, so you need to look at what he reads. In his books and many interviews, he has talked about some of the books and authors he considered important in his formative years at Columbia: Herman Melville, Toni Morrison, E.L. Doctorow, Shakespeare, Philip Roth, Ralph Ellison, Malcolm X, Friedrich Nietsche, etc. He noted Reinhold Neibuhr as his favorite philosopher. He recently positively reveiwed Doris Goodwin's "Team of Rivals: The Politcal Genius of Abraham Lincoln." A fairly conventional list, to the left, but mainstream.
If you want to know who is influencing his ideas, look at his actual advisers, not people he shook hands with to make political deals. He is known to consult with a wide variety of people on the big issues, (none of whom are noted by the McCain campaign in their constant guilt by association campaign.) As for his actual policy advisers, apart from the big names like Warren Buffett, Colin Powell, Zbigniew Brzezinski, etc., on a daily basis he surrounds himself with a team of slightly leftist but mostly non-ideological pragmatists. It is very different from the team of big idea guys that Pres. Clinton surrounded himself with.
Here is a rather long article that notes what I have seen in many places: his very pragmatic approach to issues.
Money quote: "...As opposed to the ideological Clintonites, the Obama wonks tend to be inductive--working piecemeal from a series of real-world observations. One typical Goolsbee [Obama economics adviser] brainchild is something called an automatic tax return. The idea is that, if you had no tax deductions or freelance income the previous year, the IRS would send you a tax return that was already filled out. As long as you accepted the government's accounting, you could just sign it and mail it back. Goolsbee estimates this small innovation could save hundreds of millions of man-hours spent filling out tax forms, and billions of dollars in tax-preparation fees.... Think of the contrast here as the difference between science-fiction writers and engineers. Reich and Galston [Clinton's advisers] are the kinds of people who'd sketch out the idea for time travel in a moment of inspiration. Goolsbee et al. could rig up the DeLorean that would actually get you back to 1955."
And: "The Clintonites were moderates, but they were also ideological. They explicitly rejected the liberalism of the 1970s and '80s. The Obamanauts are decidedly non-ideological. They occasionally reach out to progressive think tanks like the Economic Policy Institute, but they also come from a world-- academic economics--whose inhabitants generally lean right. (And economists at the University of Chicago lean righter than most.) As a result, they tend to be just as comfortable with ideological diversity as the candidate they advise."
Everything that I have read from serious sources indicates Obama's deep pragmatism and light take on ideology. Here is a quote from his second book, The Audacity of Hope: ""I think my party can be smug, detached and dogmatic at times. I believe in the free market, competition and entrepreneurship, and think no small number of government programs don't work as advertised ... I think America has more often been a force for good than for ill in the world; I carry few illusions about our enemies, and revere the courage and competence of our military. I reject a politics that is based solely on racial identity, gender identity, sexual orientation, or victimhood generally. I think much of what ails the inner city involves a breakdown in culture that will not be cured by money alone, and that our values and spiritual life matter at least as much as our GDP." - It is a very pragmatic, even conservative approach (in the Burkean sense.) To me, he appears to be a fairly moderate liberal, but a liberal who has taken on board the intellectual critique of 60's liberalism by the conservative movement.
In contrast to that is a man who served his country well as a Naval Officer. As a Marine combat veteran I appreciate that, but I also know that it doesn't necessarily mean that he should be in elective office. He's a hero, fine. But he freely admits that he doesn't know much about economics. He, in fact, has never been regarded as a particularly strong intellectual force in his party in the way that Dick Armey, Newt Gingrich, or Orrin Hatch were.
He consistently reacts viscerally to events. He consistently seeks to understand issues, all issues, in terms of white and black. He only wants to know who the villains are, so he can "fight" them. His only reactions during the banking crisis were to seek out who to blame so he could seek to have them punished. His very simplistic call for "victory" in Iraq is another example, as if any of us know what "victory" is there. I fought there for a year and I certainly don't know. But he does. Just ask him.
No, I have had enough of this unthinking reactionism that only seeks enemies to lash out against and can't understand a world of grey subtlety and complexity. McCain's very irresponsible choosing of Gov Palin, who is obviously unready to perform at the national level, is just one more example of McCain's gut decisions, and a perfect demonstration of how they can so easily go wrong. I voted against John McCain as much as I voted for Barack Obama.