Trump's so pleased by his wit, it never occurs to him that people around might not think it as witty as he does. So he would never consider it offensive, because to him, it was inclusive, he thought he was honoring them by being relaxed and fun loving, giving 'em the warm and fuzzy Donald.
I think it occurs to him.
It's a neat trick to say something crude followed by the word "but" followed by a nice sentiment, and he does it quite a lot. Saying "Pocahontas" even after he's been told before that it's offensive, and then very immediately following it up with "but I like YOU!" is a great example of his trick. He does it so, when people point out he said something mean, he can say "No! didn't you hear that I said something nice!"
However much or little conscious awareness goes into it, the "get out of jail free" card that he always includes just in case his wit hurts someone shows he's got some awareness that his "wit" is offensive.
The word "Pocahontas" is not inherently offensive. There's even a Disney movie with that title.
While you could argue dismissively calling an Native American woman "Pocahontas" might be offensive, that's not what Trump did. He called a white woman who claimed to be Native American "Pocahontas" to make fun of her for being a liar.
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