"Cali out" on the topic? One can only hope. Obama is not "actually black, racially or in terms of experience?" Now I know you like to define terms in your own way, but this is a stretch. "Black" is kind of a weird word, as it doesn't describe the color of most people's skin, or barely any. But African-American makes sense, and he clearly is. Plus, you have no idea what it is or has been like to live in his skin, and I'm sure you haven't read his books, so you lose that point.
His middle name is Hussein. It just is. Why shouldn't he keep it? Or why should he deny it? I don't know that it shows a "sweet spot" for Islam, but his life experiences could imply a generosity of spirit to another culture and religion. That's not a bad thing. Particularly in a world leader. You, however, display a great distain for an entire group of people in your Islamophobia. So I don't think you get points for that one, either.
"...as if Obama himself is a serious person or a serious intellect of any kind." Hmmm. I don't think you're going to get a lot of takers on that one.
As to underestimating Trump, and the seriousness of his candidacy? Plenty of people would have lost money on that bet, but it's not incumbent on the Democrats to deal with it, yet. It's the Republicans that are freaking out. Obama was hitting a big and easy target at a roast. I think it was all in the spirit of the evening.
First things first. Like Federberg, you are completely ignorant about Islam. Have you ever read hadiths? Have you ever read Ibn Ishaq's biography of Muhammad? Have you ever read any Islamic jurisprudence? No, no, and no. If you did, you would see that it is entirely rational to have concerns about massive Islamic immigration and jihadist doctrine (not to mention the massive wealth of evidence provided in the last 15 years of what is going on in the world). When it comes to Islam and many other topics, your problem is simply ignorance and cultural illiteracy. You lack knowledge, plain and simple. There are some ways in which "fear" makes sense and others in which it does not. As the Europeans have learned in recent years, there is ample reason to have concerns about Islamic immigration. That is the rational position of well-informed, well-read, well-educated, and knowledgeable people, a description which disqualifies all members of the Democratic Party in the United States.
As for the middle name. The problem is that Obama has made a claim throughout his life to being a Christian. No serious Christian would ever keep that name. If you know people from India, for example, you would know that when their families convert from Hinduism to Christianity they almost always adopt Christian names. And they do this without Hinduism being a historic rival to Christianity either. By keeping his middle name as that of the son of Muhammad's cousin, Obama is making a very clear statement about his lack of conviction about Christianity and his cultural affinity toward Islam. Muslims don't go around with names like Mohammed Peter Al-Abadi. This affinity is in many ways hypocritical (Islam does not condone his beloved LGBT movement), but it still shows where his prejudices lie.
Third, Obama spent his formative years in Indonesia, as Carson pointed out. He claims that he spent his youth as an oppressed black and that he relates to the black experience. This is laughable. How do you relate to the American black experience if you are in Indonesia as a child? I doubt that you as a white female from Maryland would say that you relate to the Arab female experience of Omanis and Qataris. Although, with your beliefs, you would probably get thrown into the Gulf of Oman and we would never hear about you again. The religion of peace would do a job on you.
Furthermore, Obama has been coddled and celebrated his entire life by white leftists like yourself. His career was made for him. He went into fields of study where the left predominates and his identity would be celebrated. People like yourself feel decent, moral, and wholesome at the sight of Obama. He provides you moral self-justification and makes you feel like you are a nice, "generous" person for supporting him. He is the ultimate multicultural symbol for whites who have rejected their Christian heritage: he is biracial and he bears a middle name from the religion that has been Christianity's greatest historic enemy. Couldn't be better, could it? Obama has been told his whole life by white leftists rooting for him that he is brilliant and articulate when he is neither. When he is talking off the cuff, he constantly stutters and searches for words, almost as much as Bush even. In his recent interview with Chris Wallace, he used the words "basically" and "stuff" in the space of about 8 words. I don't think this is an indicator of a highly educated orator.
As for being generous toward other groups, Obama is just as culturally illiterate as the retarded Bernie Sanders supporters. He does not know any foreign languages and he clearly has no familiarity with the greatest works of history and literature that created the civilization he is riding the coattails of. Hopping on planes, eating at dozens of McDonald's, and going to shake hands with foreign leaders doesn't make you cosmopolitan. It just means that you are using modern transportation. It's easy to get some artificial friendly looks from foreign leaders when you are sitting on the greatest arsenal of weapons of mass destruction the world has ever seen. That is nothing to write home about.