You are criticising Obama on 'remarks' taken out of context, and to which you are creating new and false context.
"Bitter remark": For one thing, Senl. Obama did not make the "bitter remark" in front of a "more or less well heeled group"; but made it in front of a rally of an extensive demographic. And, in context, he didn't say that lower or working classes were bitter because they were lower or middle class, but that in their bitterness at situations created by the present administration, were turning to those things in which they could trust, including their religious beliefs and their rights including those protected by the Second Amendment. He did not say that they were more bitter than other classes or groups, or that they were only (or only could) turn to religion and guns. Read or watch the speech, not just the sound byte.
"Lapel pin": Did you know that it is inappropriate and a breach of flag etiquette to wear the American flag except as part of an official uniform. Look it up; many flag web sites. But, beyond that: I also think that "lapel pin patriotism", is a straw man/red herring, meant to denegrate in the absence of any substantive criticism.
Michelle Obama's comments: Besides the fact that her off the cuff remark didn't spell America with double Ks; while somewhat embarrassing, does reflect a minority's exclamation of finally feeling proud to be included in what I often heard (and I'm sure you've heard) that "any boy can aspire to be President of the United States." Up until this campaign, no black person, and no woman, could actually say that (and notice that the phrase uses the term "boy") with any justifiable claim that such a circumstance pertained to them. We have come a long way, in race, religious, and gender tolerance and equal treatment, but the very fact that the questions of race, gender, religion, etc. keep coming up tells you that we have a way to go; and that Martin Luther Kings aspiration of a time when the quality of a persons character was more important than the color of his/her skin still has not arrived.
Rev. Wright: I don't know, but I have attended churches, synagogues, taken college courses from, and hobnobbed with preachers, rabbis, and professors who both expressed questionable positions with which I both agreed and disagreed; and they have remained, up to a point, my friends (on occasion), mentors, and confidants. I don't, and I don't expect anyone else, to surround themselves with only those who either agree with me, or are PC or acceptable to the majority of those around me. Oh, and yes, as regards Ayers: I have radical friends, either radical in the past and have become less radical, or remained consitent in their radicalism, of both the left and the right.
Hillary out spent and tried harder: I don't deny the Sen. Clinton was outspent by the Obama campaign; but I find no evidence that she tried harder than Sen. Obama to speak to the working class whites, or to Hispanics, or to any other group or class than did Sen. Obama. What she did do, effectively, was to characterise Sen. Obama, and (I believe) to appeal to pre-existing prejudices. Saying it more simple: She was more effective in labeling Sen. Obama as an eletist than he was in communicating his concerns. I don't think that it was a matter of substance; but, rather, a matter of her being a better connector to their prejudices.
Now, I do listen to NPR, but I don't conform to your other sterotypes. I don't think that my vote is more important than anyone elses, but neither did or does Sen. Obama. And, I'm not second guessing any one's motives; but I also do not believe that any one has a substantive reason to believe that Sen. Clinton had or has a more sincere connection to or concern for the working class (white, black, or other) than Sen. Obama, or that her programs or policies spoke more to their desires or needs. In a nutshell: Sen. Clinton spoke to prejudices, and created distinctions that did not and do not exist.