The US Elections: Barack Obama
Experience and ability When he initially declared his candidacy, I didn't think he had a chance as he hadn't even completed a term in Senate. But in winning the Democratic nomination against overwhelming odds (ie running against the presumptive nominee), he's shown he has the ability. Thus he will be capable of getting things done but his lack of experience means that he will likely make more than a few mistakes along the way.
Pallin' around with Ayers, Rezko and Wright: I am not concerned that Barack had associated with an unrepentant (albeit incompetent) terrorist, a corrupt bagman and a hellfire preacher. What does concern me is that he has been unable to provide a convincing narrative to create distance between himself and the unattractive aspects of the unholy trio. Simply saying about Ayers something like "We all regarded him as a nut for what he did and avoided speaking to him about it for fear of receiving yet another lengthy tedious monologue but when it came to education he had some very good ideas" would have done much to quell any concerns. Likewise Rezko could be explained away with "You needed to know such people in order to get anything done in Chicago, sad but true" and Wright with "I generally tuned out during his sermons". The fact that he has not yet done so makes me wonder whether he is psychologically able to do so.
Joe the Plumber: What strikes me most about the Joe the Plumber incident is how unnecessary it was. Joe simply asked about how Obama's tax plans would affect his intentions of owning a small company. It wasn't as if he was indicating a desire to become the chairman of a large multinational. All Barack had to do to say that his tax plans wouldn't be affecting small businesses amongst other political fluff and nobody would have been any wiser. But in giving the answer that he did, Barack needlessly created a potential opening which still rumbles on.
Joe the Gasbag: In my opinion the worst decision that Barack has made was the choice of his vice-president. I believe his decision not to choose Hillary Clinton was the right one as after bungling the healthcare reform and the 2008 democratic primary, no sane person could dispassionately want her in a position of power and responsibility. Yet choosing Joe Biden was an uninspired choice that it seemed to show a lack of imagination (and made the choice of Sarah Palin even more dramatic). If he had chosen somebody with a slightest bit of colour, like say Governor Bill Richardson (executive experience, hispanic, former ambassador to the UN) I would feel a lot more comfortable.
The lack of a killer instinct: Sometimes in politics, you have to be unpleasant to people. John McCain had this beaten into him by North Vietnamese Torturers. Hillary Clinton has learned this the hard way through her marriage. But with Barack, I don't see anything in his political career or personal history that indicates that he can do this or even knows this. He singularly failed to put Hillary out of contention for the Democratic Primary for example.
So if he does become president, I fear that we are going to see a fair amount of missteps during his term.