It pains me to say this, but humor seems to take a backseat in this article, along with "the angle" that you are trying to accomplish. For example, are you writing this from the view point of someone who is in awe of Obama, or just someone who can't cut the guy some slack? Where I see "stabs" at humor, they miss. I would refocus on satire and parody, and throw in the occassional the nonsequitor.
Poking fun at leaders is a good thing. And Obama is hard target to poke at because he's such a straight shooter and George W. Bush was such a fuckwit. But I would like to see more work done on accomplishments (like the Obama bump, getting borderline racists white people to see beyond his color, mainatining his cool while John McCain went all alzheimer on him, Not laughing at Sarah Palin in public and not taking her bait, etc.)
Prose and formatting:
The prose is very, very good. What keeps it from getting a higher score is that the prose is also very dense. You've packed a lot of information packed sentences into this work, and they may be too "thick" for the average Uncyclopedia reader.
The images seem rather stock, and blah. One image that doesn't work is the Hitler image, which seldom work in all but a very few instances. Yes, the right wing nut jobs like Ann Coulter (Adolph Hitler's love child) hated Obama. But can we do better than Hitler?
You get points for taking this on. But I think you need to take it back and work some more on this. I would also do the following:
The first mention of the article's title in the opening paragraph is ALWAYS in bold.
It is Senator John McCain (R-Arizonia) and Gov. Sarah Palin (R-Alaska) when referring to these people in the first instance, their Presidential and Vice Presidential aspirations are mentioned secondly.
More wiki-links throughout will help. You have passages with no linkification. Select the links carefully.