For what it's worth you have to do awfully as President; or be seen as an awful campaigner (George Bush snr) to get challenged. There was talk of a Jesse Jackson challenge to Clinton in '96, there was suppose to be an anti-war candidate against Bush and some die-hards wanted to go after Obama.
The thing with Trump is that after winning both elections he'll be seen as being very effective; all depends on what his Presidency is like though
I think the political environment has changed since then. Presidential campaigns serve to help people promote themselves and get publicity for their ideas.
Obama avoided a challenge because he had broad appeal to the party, and because no prominent Democrat wanted to hurt the career of the first black President. Trump has no such advantage.