Trump's implied allegation, that Obama is/was "too stupid" or "not a good enough student" and thus is a bad President and/or unfit for a second term is a pure straw man argument. The only place you can make an argument like that and have people believe you is in the media, where fact-checking and ethics have become woefully absent. In any legitimate debate or discussion Trump's implied allegations would be dismissed completely.
That's kinda the whole point: Trump can spout illogical bullshit all day long and the media will print it without fact-checking b/c it pushes papers, eyeballs, and clicks and the American populace will eat it up. If it's on the news it must be true! N/m that it's 100% bullshit...
For one thing, this is not a "pure straw man" argument. A straw man argument is something different.
For another, the media cannot "fact check". Obama has not released his academic records so there's nothing to fact check to.
I also think you miss the point of what Trump is doing. While Trump may be many things, he is not entirely stupid. He knows to use the media, and he knows how to exert pressure. And he knows that if left uncontested some people will believe the allegations. He knows that very well IMO. I also think he knows that the Obama team knows that too.
Obama himself boasted many times that he will transparent etc. He has not been, very few argue that. So, Obama left himself open and Trump is moving to take advantage of it. It has been noted many times that Obama, by being a relative unknown, let himself become a blank canvase that people could paint on it what they wanted. Trump is using same principal to his advantage. Obama's failing to release his academic records leaves us with a blank canvase and Trump is stepping up to paint it as he wishes. Trump is painting a negative image (AA student etc) and may force Obama to release those records (if he can) if Trump's (unflattering) picture gains traction.
If Trump manages to get Obama to release the academic records, that'll be the second time "The Donald" has forced/manipulated him to do so. That puts Trump in a strong position and Obama in a weak one. Is he showing us Obama is a weak player we don't want representing us in foreign affairs? Is Obama being outplayed/manipulated by others just as Trump is doing (or may do)?
I contend you're seeing the 'art of the deal' here, a demonstration of 'negotiating'.
It's long been held that when a lower player (Trump) can mange to force a higher player (Obama) to engage them, the lower player gains big. The higher player wants to ignore the lower player; Trump's beaten him once.
Fern