The fivethirtyeight blog is pretty good on non-conventional insight.

I've had two major complaints with Obama's campaign: 1) playing defense all the time, not hitting first (via free media Ads with no money behind them) and 2) the consultant class schlock that Obama's media people (Axelrod?) put on TV.  

http://www.fivethirtyeight.com/2008/09/o bama-needs-more-better-ads.html

One of the more disappointing elements of the Obama campaign has been their advertising, which has tended to focus on fairly conventional, 30-second, issue-based spots. Their ads have been neither creative nor attention-grabbing, in contrast to both their reputation for being a media-savvy campaign, and some of the relatively creative spots put together by the McCain team.

I suspect that the next 2-3 weeks are probably the most important point in the campaign for advertising. Once the debates begin, it will probably be too late to fundamentally redefine either the candidate's message or the opponent. And advertising is difficult in the two-week home stretch between the debates and the election, with campaigns usually constrained to conventional biographical spots or hail mary negative attacks. So now is the time for the Obama campaign to go all out and spend some of those hundreds of millions of dollars in donations they have collected.

I've always said that Obama could pull an ad from YouTube or comedy central put his "approve this message" stamp on it and have more effective ads than what he's done so far.