[Note: this is a prediction, not advocacy.]
I see two trends in Presidential elections among the Democratic and Republican nominees:
1. The ticket with the most Ivy League degrees wins. (The Ivy League is Harvard, Yale, Princeton, Columbia, Dartmouth, Cornell, & Brow;n, although half of them aren't mentioned here).
2. When there's no incumbent, the more outsider-ish candidate wins.
Here's the evidence.
1. The first list is updated from July. Here are the universities that the Presidential and Vice Presidential nominees since 1980 attended. If two schools are listed, the first is the undergraduate school. The Democrat is on the left, the Republican on the right. The winning ticket is in italic. Ivy League schools are in bold. Data from before 2004 and earlier is copied from this 2008 blog post.
2016: Wellesley, Yale (law) v. Pennsylvania
vp: Missouri, Harvard (law) ??? v. Hanover, Indiana U. (law)
2012: Columbia, Harvard (Law) v. Brigham Young, Harvard (Law, MBA)
vp: Delaware, Syracuse (Law) v. Miami (OH)
2008: Columbia, Harvard (Law) v. Naval Academy
vp: Delaware, Syracuse (Law) v. Idaho
2004: Yale, Boston College(law) v. Yale, Harvard(MBA)
vp: NC St., North Carolina v. Wyoming
2000: Harvard v. Yale, Harvard(MBA)
vp: Yale v. Wyoming
1996: Georgetown, Yale (law) v. Kansas
vp: Harvard vs. Occidental
1992: Georgetown, Yale (law) v. Yale
vp: Harvard vs. DePauw, Indiana (law)
1988: Swarthmore, Harvard (law) v. Yale
vp: Texas v DePauw, Indiana U (law)
1984: Minnesota v. Eureka
vp: Marymount Manhattan, Fordham (law) vs. Yale
1980: Naval Academy v. Eureka
VP: Minnesota v. Yale
2. Here's updated information from a 2008 post. An "outsider" is considered an outsider relative to the other candidate, usually a governor or former governor with little to zero experience in Washington. They don't usually win against an incumbent, but always beat non-incumbents with more DC experience.
2016: Outsider vs. Insider: Winner: ?
2012: Outsider vs Incumbent. Winner: Incumbent
2008: Outsider-ish (short-time Senator) vs. insider (longtime Senator): Winner: Outsider
2004: Insider (longtime Senator) vs. incumbent. Winner: Incumbent
2000: Outsider vs. Incument VP. Winner: Outsider
1996: Insider vs. incumbent. Winner: Incumbent
1992: Outsider vs. incumbent. Winner: Outsider
1988: Outsider vs. incumbent VP. Winner: Incumbent VP
1984: Insider (recent VP) vs. Incumbent. Winner: Incumbent
1980: Outsider vs. incumbent. Winner: Outsider
1976: Outsider vs. incumbent. Winner: Outsider
1972: Insider vs. incumbent. Winner: Incumbent1968: "Outsider" (former VP eight years removed from DC) vs. incumbent VP. Winner: Outsider
Based on these trends, the election between Mrs. Clinton and Mr. Trump looks like a toss-up. Her ticket has more Ivy League degrees, and Mr. Trump's is the outsider. In fact, his"outsider" status is a little too outside in that he's held no elective office or had any government experience at all. Only Wendell Willkie in 1940 is similar, and he lost to the incumbent.
On the other hand, Mrs. Clinton is herself four years removed from holding any office. If her opponent was a sitting Senator, she would be the "outsider" of the two.
So who will win?
What it comes down to is I see no reason for people who voted for Mr. Obama in 2012 to not vote for Mrs. Clinton. They may be disappointed that a seemingly less shady person like Joe Biden didn't run and get nominated instead, but concern about Mrs. Clinton's ethics likely won't cause one to switch to Mr. Trump, who has his own ethics issues.
There's really nothing that transpired in the last four years to change one's mind about Mr. Obama or the Democratic Party that wasn't known in his first term, and there's nothing about Mrs. Clinton that represents a radical departure.
So if this is about "Obama's third term," Mrs. Clinton has the advantage. The only counter-argument is that Mitt Romney failed to inspire Republicans who failed to vote in 2012 and Mr. Trump may attract them. At the same time, he's lost other Republicans and there is now a stronger third-party and fourth-party presence on the ballot since 2000.
My guess is that Mrs. Clinton wins. But I don't bet.