What would it take for Trump to win?
A few things.
1. Social unrest.
2. One or more major 'terrorist' attacks.
3. Making Trump look like someone with reasonable/achievable ideas, and/or discrediting the opponent.
ad 1) The republican members of congress have successfully undermined the belief of the people in Government, by blocking just about any change for the better, and promise to reverse those things that did pass (like Obama's version of healthcare that was proposed earlier by some Republican states). People do not believe Government is there for them, so they will support anyone who claims that the people must make America Great again, the populist's agenda.
However, since isolation is not the answer to globalization, that will create an even larger loss of faith in what a proper government can achieve, not only for the most wealthy, but especially for the middle class (largest consumer base), and humane solutions for the underprivileged.
The Republican party's strategy has created it's own monster of Frankenstein.
ad 2) Insecure people look for 'strong' leaders. It doesn't matter if unachievable solutions are promised, just an appeal to primitive feelings (i.e. xenophobia) will suffice.
ad 3) For this he has already appointed
Paul Manafort, someone who already successfully helped to get Ferdinand Marcos, Jonas Savimbi, Viktor Yanukovych, and other foreign dictators elected. If anyone can polish a turd, then he is the man. In March 2016, as the potential for a contested convention increased, Trump hired Paul Manafort, who has worked in presidential politics since the 1976 Republican convention, as his convention manager
Cheers,
Bart