I think it matters a great deal more who stands with, and behind, the person in the Oval Office.
In 2000, George W. Bush was perceived as a likeable fellow, the sort of man one would want to have a beer with, as opposed to the Harvard-educated policy wonk, Al Gore. But how many Bush voters understood that they were voting for Rumsfeld, Wolfowitz, Halliburton, and Blackwater? How many fiscal conservatives perceived that they were voting not only to spend the Clinton surplus but to rack up the biggest federal deficits in history? How many folks irritated by Bill Clinton's military adventures in Kosovo and Bosnia knew they were voting for eleven years of war?
Above all, they were voting to take money out of their own pockets and give it to Wall Street speculators euphemistically called "investment bankers". They were also voting to gut Social Security, although Democrats in Congress stopped that from happening.
To me, it matters less who lives in the White House than who forms the coalition of which he or she is the figurehead. Take, for instance, teachers. I'm all for empowering teachers; I believe strongly in public education and feel even more strongly that teachers are far more likely to know how to build strong schools than are politicians or lobbyists. Congress should not be in the business of telling teachers how to do their jobs, and any candidate supported by teachers is likely to get my vote. A candidate backed by Goldman Sachs, on the other hand, I will always be suspicious of. It has been many years since these people did anything that qualifies as investment, as opposed to speculation; they are essentially parasites. They are takers, not makers, and will demand their pound of flesh from anyone they help elect.
A question that has been much on my mind lately, as I read myriad posts here extolling the virtues of Bernie Sanders and others faulting him, is whether anyone can be elected President without making deals with devils. The consequences of Citizens United stretch deep into American politics, after all. There is a little AM radio station I do some work for that runs frequent ads for various right-wing pressure groups promoting such things as "free trade". Decades of "free trade" have left us all the poorer, and I am not inclined to vote for any candidate backed by its proponents.
Yet it seems the media care mostly about personalities: can you trust X? isn't Y a clown? does Z have the requisite experience? is Q too old? and so on. I am much more interested in knowing who is behind each of them. That's how we will know a candidate's true colors, and what we can expect from him or her in office.
But perhaps your mileage varies.