And I believe Bastard's whole point with the comment you quoted was that they were using it to essentially talk down the president as though he didn't deserve his job based on race. I don't agree with his point 100%, but I at least understand what he's saying.
That requires a lot of interpretation and reading into Donald Trump's remarks something that was arguably never actually said or implied.
Asking "how did Obama go from crap grades at several schools and colleges to being Magna Cum Laude at Harvard" is simply shining a light on a questionable part of Obama's past that the liberal media didn't want to investigate. Obama did drugs, and may have even sold them. It is not clear how Obama, initially not a great student, got into Harvard, or how his education was paid for. All things that could reflect negatively on Obama, and reveal unflattering connections, and perhaps even more radical connections than have already been revealed.
Obama is one of the most unqualified men to be elected president. He was given a free pass. It was essentially an equal opportunity nomination. He was a U.S. senator for barely 2 years before announcing his candidacy for president. That's it. That's all.
Colin Powell, or Herman Cain, or Clarence Thomas have EARNED their position in society. Obama was handed his. Given an Oval Office and nuclear football just for showing up. He is the ultimate unqualified token hire. Even his Democratic nomination was determined in a back room, and was not the clear choice of 2008 Democrat primary voters nationwide, but the choice of an elite group of convention delegates who decided they liked the idea of running a black guy as their candidate, despite Hillary Clinton polling higher among voters.
Sarah Palin, by contrast, derided as "scary" and unqualified by the liberal media, was a very effective and popular governor, a lieutenant governor who courageously challenged the sitting Republican governor of her state when she saw corruption, rather than towing the party line, was a mayor, was a city council member, and began her career rising through the ranks of the PTA, that initially sparked her interest in public service. I find aspects of Palin offputting, but against all partisan derision, she is unquestionably qualified. Obama is not.
Obama was clearly not qualified, but the press selectively omitted any vetting of facts that would hurt Obama's candidacy. Obama was radical (Frank Marshall Davis, Wm Ayers, Rev Jeremiah Wright, Andy Stern, Cass Sunstein, ACORN, SEIU...) but the media --against the easily traceable facts-- allowed Obama to deceitfully be portrayed as a moderate. And as soon as he took office, the true radical made himself manifestly plain to see. But media coverage allowed Obama and his radical puppetmasters to be elected and inaugurated unvetted.
That is precisely what Trump is exposing through his political rhetoric.