In thinking about this, and scratching my own head to try to figure out the guy's secret sauce, it struck me that there's a small but importantly nuanced difference in the two campaigns. I went to both websites which to me act as reflection of their public positioning quite well.
Hillary talks about the issues, and how she'll tackle them. It's pragmatic, and seems thorough and is perhaps a little un-exciting. She's drawing a picture of America's issues and what she will do about them. If the question in the voter's mind - their mindset - is show me your plan..then she has it nailed.

Here's we see that he'll make America great again. He paints a picture of a positive outcome that is admittedly very very light on details. So - if the voter's mindset is 'Show me your plan', his position overall is weak. I think that's been a commonly concluded fact that most of the media is well aware of about his campaign.
But the small and fundamental difference here is applicable to those who DO NOT have 'the show me your plan' mindset. Now, we see Hillary talking about problems, and Donald talking about positive end-states. Hillary doesn't think America is great today, and by electing her, it may never be if all her detailed plans don't work out. Donald is aiming to have the country great...and regardless of the bits between today and getting there - that's not a bad place to aim. Arguably, it's an enviable place to move towards. Boil it down further.....Hillary = Problems and Donald = Great
Of course the devil is in the details, and without a realistic plan nothing will happen. But in this one subtle area, Trump has Clinton seriously out politicked, and I suspect its a key piece of the positive perception he's benefitting from these days.
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