In Obama's defense, he was asked whether he ever shot a gun, he said that he shot clay pigeons "all the time" at Camp David, and then the White House released a photo of Obama shooting a gun. He didn't look like a someone who was an experienced shooter, but he didn't really claim to be an experienced shooter. And that's what the Republicans focused on during the discussion on the gun control, because it was an easy distraction.
In Trump's defense (can't believe I typed that), he has never, ever tried to appear working class. His whole brand is high-rolling business man. He is also white trash, which tends to have some overlap with the "white working class" voting block. He genuinely likes professional wrestling, McDonalds, and fucking anything that moves. He is racist, sexist, and profoundly ignorant. Playing around in a tractor cab was just playing. His bullshit is always geared at looking wealthier than he is. Well, and pretending to be religious.