Thanks for the thoughtful post, GammaBoy. While time prevents me from providing a point by point rebuttal, I will offer a couple of thoughts.
First, I think it's interesting you seize upon this report as being indicative of Obama's character because there is this incident, which received absolutely zero MSM play. In the first instance, Obama made it clear he was a White Sox fan and never said he was cheering for the Ray. In the second instance, you have a candidate pandering in the telling of a story that is central to the candidate's entire mythology. Just something to consider.
Second, the old political and war veteran has been anything but a steady hand during this election. He has flipped flopped on so many issues (the Bush tax cuts, offshore drilling, social security privatization, and the list goes on) that the campaign was unable to push Obama's own waiving on offshore drilling and nuclear power. And many of his campaign's critical decisions appear to have been hastily made, which have made its candidate appear erratic. Chief among those decisions is the Palin pick, which earned a temporary boost, but has caused long-term damage to the ticket. This poorly considered decision has drawn criticism from well known conservatives from David Brooks and Peggy Noonan and even caused the likes of Christopher Buckley, Andrew Sullivan, Christopher Hitchens, and Colin Powell to support Obama. Even if we don't drill down on the whole "I'm canceling the debate" debacle, McCain has looked unsure and unfocused during this election cycle.