There are some good bits and I especially like the diary entries. However, I feel the humour is too focused on his race and drug use, especially the drugs use. Some of these bits could be much better, if they satirised his obsession with change and hope, or other idealisitc ideas.
Well, obviously we need an article on him.
Prose and formatting:
I didn't notice any errors here.
I didn't really like the Barackstar picture. There was an excellent caption on one picture where it suggested he might be stoned out of his mind. This was the one drug reference I really liked.
I don't like the Iowa caucus section, mainly because it is immediately dated. Trying to keep up with current events is going to be a lot of work, so I'd suggest using some dramatic irony and claim the win in Iowa is certain to propel him to the presidency.
There is a good basis here, but there needs to be more satire on Obama the vaguely idealistic political everyman and less on Obama the drug-taking black guy. It's pretty egotisitical to link to my own political article for inspiration, but here it is anyway.