I don't think that he has the least degree of difficulty tailoring his message to others, regardless of their personal philosophies.
He can change position in an instant whenever it suits his purpose. This is why he has been both pro and anti abortion rights, a racist and not a racist, etc.
He feels no need to be truthful or compunction about lying at any time, so changing his position has no internal cost. This was made clear by Stephen Schwartz, the man who wrote "the Art of the Deal" for Trump, in an interview in the New Yorker:
“He lied strategically. He had a complete lack of conscience about it.” Since most people are “constrained by the truth,” Trump’s indifference to it “gave him a strange advantage.”
“Lying is second nature to him,” Schwartz said. “More than anyone else I have ever met, Trump has the ability to convince himself that whatever he is saying at any given moment is true, or sort of true, or at least ought to be true.”
“He’s a transactional man—it was all about what you could do for him.”
Trump’s need for attention is “completely compulsive,”...
He praises people who can do something he wants and disparages people who can't do something for him.
It's kind of a smear on New Yorkers to compare his raging narcissism, complete disregard for the truth and transactional, situational ethics with the "blunt New Yorker" culture.