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At this point in the American presidential election cycle, Trump supporters should be excited -- not despite the challenges, but because of the challenges. Their candidate is an assertive, even aggressive personality, a fighter. What does a fighter relish if not challenging, high risk/high reward situations? Imagine you have been summoned to Trump Tower. Can you make 'contact' and a persuasive argument that some of these challenges are central, some peripheral, some not even challenges at all? Electoral College arithmetic / Swing-state uncertainties Raising and spending money Hostile and adversarial media environment National campaign strategy and tactics "Unfavorable" opinion / Demographic change since 2012 'Lack' of conventional campaign superstructure Coordination with GOP campaign Wavering support from GOP / Unity at the Cleveland Convention "Incoherent:" policy proposals Bias, prejudice, "political correctness,: conventional wisdom I will flesh the list out in separate comments. What have I missed, what have I split, what else do you think are the top challenges for the Trump campaign? (I have re-ranked the Top Ten list, in light of feedback from members. We now have one Trump supporter in the mix!)