Yeah, it amazes me as well that such radically different impressions can exist regarding Trump, seemingly derived from listening to the same rhetoric emanating from him and his surrogates. I think rather then use the term "naive", it would perhaps be more accurate to say you trust the man far more then me, who trusts him not at all.
I perceived him to be a cynical demagogue. I see demagogues as virtually the ultimate cynics where human nature is concerned, and so, it is very difficult for me to see an extreme cynic as compassionate toward others. Family members excluded perhaps, but, as for the rest of humanity, or that portion represented by the American electorate, they exist to be wrapped around his fingers by any means needed to garner their vote. Of course, that might describe any politician, but demagogues take it to the extreme to play on the fears, anxieties, and anger present in a segment of the population.
Coupled with his extreme degree of self-involvement, he claimed yesterday without proof, for instance, that 3-5 million illegal votes went to Clinton, or else he would have won the popular vote, it's just very hard for me to see him truly concerned with much beyond his own ego gratification. So far, at least. His claim that he would have won the popular vote were it not for millions of illegal votes I guess might be described by Kellyanne Conway as an "alternative fact" perhaps. I would say he and his surrogates exist in an "alternate universe", but I don't really believe they do, as I believe there is a method to this madness and it involves discrediting the liberal universe entirely.
Evan McMullin, who ran for the presidency as a conservative candidate, put it this way: "[Trump's attacks are] intended to destroy the media's ability to hold him accountable."
I suspect he's correct, and it's very difficult for me to see this as a good thing. Other then good for Trump if he can get away with it. Since it is the liberal universe that is being damaged by the fake news phenomenon, I cannot take seriously the claims of Trump and his supporters that it is the entities most damaged by fake news that are the outlets actually creating it.