Sure thing; George W Bush also had success in simplifying his messaging.
Re: 1, I had the same question, ie predicting the average ‘intelligence’ of each candidate’s audience. I found no conclusive results in a quick study — I took a look at about 60 million Facebook comments for brevity/ avg # words, profanity, gender, etc and found that each audience was similar in all of the dimensions I looked at. But there is clearly more room for exploration in the comments sections:p
Re: 2, that’s tough. Most dimensions of these campaigns are planned, deliberate, and complicated. I don’t think that the messaging alone is what caused Hillary’s loss, it’s more complicated than that.