I like your analysis, but not sure about sophistication. You’re almost lumping it in with sophistry — the intent to deceive — or you’re making it strictly a product of class. I think sophistication can come naturally by having great experience in the subject. This usually comes about through years of education. As well, sophistication is also the quality of being complicated or made with great skill: e.g., The level of sophistication in the cameras has grown tremendously.
Yes, sophistication can have a positive or negative connotation.
But in the context of finding Trump wanting, I believe I was right to assume that the OP’s idea of a more “sophisticated” leader would likely not appeal to me.