I think you are wrong, the lack of attack against Obama has a lot to do with race! The first black president goes a long way to block legitimate criticism. The success of blocking political speech through intimidation and cowardice of the republican party and yes even some agreement on trade topics has led to where we are now.
One thing you must understand about the political establishment is the importance they put on connections and friendship in there own class, thus trillion dollar bailouts, massive stimulus programs.
Trump i believe is not anti-establishment, they do not hate him because he seemingly opposes them, it’s because up until now he was just a piggy bank to them, suddenly this ‘political cretin wants into the club’, doesn’t he know his place! Also Trump is a crude neophyte, with the sensibilities of Vinny the cat-caller stand in front of the corner drug store scream epithets at his betters and flipping the bird and shouting ‘stupid kunt’ to females who turn there nose up at him!
Money can’t by friends, but it can buy sycophants and like any celebrity Trump has those in spades!!!
I can see your reasoning why they didn't go after Obama at first (Rush was one of the few who showed guts), but its been 7 years since and a lot of other publications have no fear.