[Nov. 6 addendum below]
From all that I've been able to tell, it boils down to a few basic points, and I will provide a tally of points won as we proceed:
1. Hillary Clinton's mishandling of classified information, something she has not owned up to in any clear-cut way. Others similarly situated have faced legal of not career penalties. What might the Founding Fathers think of a president who was this careless with classified material being promoted to the presidency?
2. SCOTUS nominations. Ideologues of the left and right might love to see a Court weighted all in one direction. I've found that as things tend to go in the real world, a mix of right and left on the Court is about the best we can hope for given the kinds of decisions that judges on either side tend to reach. Or at least I think that's how many swing voters look at this as well. Under a Clinton presidency, the aging justices - two liberals, one swing vote - are more likely to retire to be replaced by a liberal judge than they would be under a Trump presidency. The unknown is which of them might die and when. As it is, the liberals have a 4-3 advantage on the court which would go to 5-3 if the next president is a Democrat. One factor that is a bit less clear-cut is how significant in the end SCOTUS decisions are, long-run, if they tend to reflect what's already a mainstream trend during their era. But all else being equal these days, I think balance is preferable to weighting to one side or other. Half a point for Trump.
3. General life wisdom/character. I'll say right off that this comparison doesn't come off well in Clinton's favor, i.e., by the best objective analysis she doesn't gain any grounds/points on Trump in this comparison. I think one would have to be a rather intellectually bankrupt (or at least corrupt if not bankrupt) partisan to think the edge is clearly in favor of the one or the other. But in somewhat more subtle ways I think the edge may go to Trump here. The main legitimate criticism of Trump temperament-wise is that he's "rude and crude," at least by the standards of career politicians who've spent a lot of time finessing their messages to avoid giving gratuitous offense to this or that constituency. The Democrats seem to have a(n otherwise reasonable) litmus test they're applying to Trump: Do Muslims have a place in Trump's American? If Trump were to improve in the area of messaging, being less "rude and crude" in that regard, he would of course explain how specifically law-abiding America-loving Muslims would of course have a place in his America. It is crudeness of political messaging and perhaps general speaking style in some respects (is being blunt being the same as being crude? Trump is I think more often blunt than crude.) that is the simpler and better explanation for his racially- and ethnically-insensitive remarks, than would be racism or ethnocentrism on his part. I think the Democratic Left has been conditioned over many years of egging-on by various Left-Wing entities (e.g., academia, politicians) to "spot" racism, sexism, ethnocentrism, a lot more hastily - i.e., carelessly - than is warranted. "That's racist!" seems to have come to be a reflexive retort on the part of "progressives" as code-word for not buying into the "progressive" narrative on race, gender, ethnicity, etc. That's intellectually lazy and counterproductive, and is often used as cover for PC/SJW agendas gone overboard that wouldn't otherwise be so loudly opposed. That's the reason that the KKK endorses Trump over Clinton; otherwise, Clinton is simply playing guilt-by-association here, and that's hard to construe as honest on her part. Likewise hard to construe as honest comment by her is her claim that Trump "demeans women" and "calls women disgusting pigs" when he's on record for having called one woman a disgusting pig. Why does Clinton abuse the language so when she ought to know better? Furthermore, it appears that Trump has been an equal-opportunity insulter, demeaner, etc., regardless of race, gender, ethnicity, etc., so there's just no clear-cut gender or race card to be played here. His (crude) remarks about grabbing women's "pussies" has not been shown objectively to be anything more than locker-room talk. That a dozen or so women who had truly been assaulted by Trump all waited to come out about that only after a tape emerged (thereby naturally generating all kinds of psychological suggestions and opportunistic motives), defies all belief. That the Democrats jumped all over these accusations as credible from the get-go - this includes Clinton and her campaign surrogates - is amazing in its own right just considering their history of smearing or downplaying accusations (that didn't all emerge at once just as a shining opportunity arose) against the male President Clinton.
As for the Clintons' character/wisdom, the wikileaks saga exposes plenty. They are consummate Washington insiders with their network of pull- and power-brokers and schmoozers. They epitomize that Washington, D.C. gravy train that a President Trump more credibly threatens than any presidential candidate in recent memory. (Obama blew his credibility on this after having pledged in '08 to change the culture of Washington.) I won't get into psychological speculations, but the inference to best explanation tells me that the Clintons seem to regard themselves as specially talented at tackling the world's problems (presupposing that their "progressive" mentality is also specially suited to that mission), and if that means having to play that very cynical Establishment game, and bend the rules as much in their favor as they can get away with, then they believe that a Greater Good which they are eminently qualified to serve justifies all that. It sounds pretty Machiavellian and the people seem to be well aware of this cynical trade-off mentality; the questions now are whether the Clintons are open and transparent with the American people about that cynical trade-off going on (all indications are that they are not), and whether the American people are fed up with that corrupted cynical culture of D.C. enough to send Trump to take that machine on.
Trump has a great family and raised great children. Even Clinton acknowledged this in the second debate when asked to name a good quality about her opponent. (Isn't she the nation's foremost political expert on children's issues? What opening did she leave for Trump with that one?) He has said some rude and crude thing involving women, but one thing I had deeply ingrained into me over the Obama years is to pay attention to what a political figure does, not to what he or she says. On the "women front," Trump has hired Kellyanne Conway as his campaign manager, and things have been going better for his campaign than before this move. He is reputed to have many women highly placed in his business ventures. On the African-American front, he is glad to have Dr. Ben Carson as a chief surrogate. On the Muslim front, Trump comes off more as ignorant than as mean-spirited; if he learns more about Muslim issues he and the country could make some progress.
Trump has said a number of things that are rather off-the-wall, things that often fail the Politifact test. An important question here is whether he says these things to deliberately deceive (an ethical and moral failing) or if he merely has a penchant for playing fast and loose with the facts, i.e., an epistemic (intellectual) failing? Either would be troubling. To be a liar requires that one know the difference between true and false and to publicly affirm the false; to be a fool would not to know the difference in the first place. I don't seriously question Trump's ethical motivations the way I do Clinton's, but I do somewhat seriously question his epistemic character. Perhaps it's crudeness of political character requiring a lot of further development, finesse, honing. Poor epistemic character in general would not so easily go with his success in non-political areas of his life. One last example on the crudity of Trump's political messaging: In the last debate (which, due to Chris Wallace's masterful moderation sensibility, objectively nullifies the noticeably weaker Trump performances in the first two debates being egged-on as he was by "media-liberal" moderators), he was asked whether he would accept the outcome of the election, and - again, not having had the chance like Clinton has to finesse his messaging for decades on end - he said that we would have to wait and see. This caused all the uproar in the "liberal media" and elsewhere, when anyone with a lick of common sense could see that were at least the question phrased a little differently - "If the process were fair and not corrupted/rigged, would you accept the outcome" - then every indication I have seen is that Trump would have answered in the affirmative. But what do I know.
So far - and I've gone to some lengths as it is just to make the point - I don't see anything here that points to Clinton as being of wiser character on the whole than Trump, and if anything there are factors that would favor Trump. I was about to award a quarter point to Trump on this one, but then comments earlier in the election season about Carly Fiorina's looks: I just can't get that out of my mind. He is a bit of a 'lookist' pig, isn't he? Playing it safe I award neither candidate points here.
(At this point it becomes more and more difficult to imagine how Clinton makes up this ground. But, just to be thorough....)
4. Domain-specific expertise. Here we are looking at expertise at doing a job like the Presidency. Trump for instance could invoke his chief-executive expertise from his business experience as one reason - all else being equal - to think he has the chops to do the job. One thing where Clinton has a clear advantage over Trump is in the rather general category of what I'll call "public policy knowledge." This is to be expected, given her many more years in the public sector and political life. She has a finessed and nuanced understanding of just about all the issues in public policy, even if not a grasp of the best solutions for those issues (which I will get to in a moment). I don't think anyone questions this about her. She does appear indeed to be a leading expert on the national political scene on children's issues. (Again, how much of an opening did she leave for Trump if she concedes that he raised high-quality children thereby setting a high-quality example?) By contrast what Trump lacks in this area he makes up for to a considerable extent in an "American can-do attitude," deal-making ability, high energy and charisma, and force of personality. He would need to rely on a lot of advice from experts in his administration, even if he does set a general tone/agenda about what goals he wants to accomplish and with what standards of excellence he wants to apply. Does "Under budget and ahead of schedule" sound like a plausible general policy tone coming from Trump? It sure would have quite an impact on the gravy-train mentality in Washington, I would think.
In the domain-specific expertise arena, a basic political philosophy or ideology necessarily comes into play. On this I cannot personally credit Ms. Clinton or award her points on the basis of her ideology being a "progressive" one. I am not a progressive myself; based on my own extensive research into political philosophy and political economy, I would fall squarely into the category of a laissez-faire individualist or libertarian. Ms. Clinton represents the Democratic Party mindset. That mindset is very public-sector oriented. Of the two major parties, the Democrats are more the party of the public sector than the Republicans, and quite clearly so. (Just ask those in the public sector unions, after all.) This is not to make a value judgment; it's just a description of the nature of the major parties. The public-sector and Big Labor interests want to see to it that the influence of corporations or other large private-sector entities is fairly balanced against the interests of labor, the more vulnerable, etc. At least that is their intentions. I don't question the intentions of the "progressive" movement on matters of public policy. I do quite severely question the results. For example, Ms. Clinton's party declared a "War on Poverty" 50 years ago; they built a sizable civil service staffed by and large by like-minded public-sector Democrats, implemented in concert with mostly Democratic big-city administrations and public schools run almost overwhelmingly by Democrats. The result, on the other hand, has been disappointing just on its face: the U.S. poverty rate is not much changed from 50 years ago. The Democrats' version of accountability on this has usually been to shift blame or to massage the numbers so as not to look so disappointing. What they don't seem to address much, is the epidemic in poorer and minority communities of single-parent families. (Would the nation's leading political expert on children's issues like to weigh in on that, at some point?) What the Democratic Party in general doesn't seem to address much is a principle that is likely more integral to the founding doctrines of this country than any other: individual freedom. I cannot name the last time I heard a Democrat praise the virtues of individual freedom. They have been more in the business of drawing a contrast between their general moral and economic vision and those of Republicans, and their vision involves bigger government, more wealth redistribution, and so on. I am far from convinced - indeed, the evidence I've encountered appears to go the other way - that progressives, Democrats, those on the Left, including those in the academy, have done a decently thorough job of exploring the greater-individual-freedom alternative. (Can they provide clear and convincing counter-arguments to the combinations of moral and economic insights provided by such laissez-faire thinkers as Rand, Mises, Hayek, Friedman, and Nozick, just for starters? Did these thinkers somehow fall short themselves of doing a decently thorough job of exploring the non-laissez-faire alternatives? The evidence I've seen points just the other way.)
Ms. Clinton would imprudently shift the balance of the court left-ward, a point already mentioned but it is part of the "domain-specific expertise" package. Also included in that package is Ms. Clinton's self-undermining assertions to expertise based on her experience at the State Dept. - self-undermining for how she blatantly mishandled classified material.
Trump has no policy record to go on. He has no experience in elected office. These are not things we can go on to assess his domain-specific expertise. We can look at how he has formulated policy proposals for some amount of insight in that regard. Earlier on in the campaign season, he was floating ideas such as "take out the terrorists' families" or "bring back waterboarding and a whole lot worse" (or perhaps even more embarrassing, the idea of punishing women who obtain abortions along with punishing the doctors). Or, indeed, the blanket "ban on Muslim immigration." In recent months he appears to have done less in the way of floating toxic policy prescriptions, and one should probably credit Kellyanne Conway for that.
I say the expertise issue is close to a wash all things considered, although I do recognize that the crucial swing voters in this election might not share my ideological enthusiasm for laissez-faire policy over Clinton-style policy. Trump-style policy doesn't seem to be considerably more laissez-faire then hers, nor do I see such policies being on offer by the major parties all that soon. What voters are looking for is the best person for facing and managing the nation's problems as they exist now. But does Trump pay more attention and respect to the importance of individual freedom than Clinton does? I think so. I'm not saying that he has a well-developed political philosophy to speak of, over and above a patriotic "Americanism" and the sorts of common-sense values that made America great (at the forefront of which is individual freedom). I am saying that by virtue of not having a deep-seated ideological doctrine he at least doesn't offer the unpalatable (for me) one that Clinton does. On the other hand, he also has spoken about going a more protectionist route with respect to Chinese imports. All I know is, Trump wants to have a "winning" attitude and temperament, but protectionism is for losers and chokers.
In terms of specifically-political managerial competence and expertise, my "gut" tells me Clinton, but my rational part tells me that Clinton blatantly screwed up in her handling of classified material, and her ideology favors expansive government over expanded individual freedom. And her shady and cynical behavior as part of the Clinton Political Machine is somewhat difficult to extricate from questions of her political expertise.
How is one supposed to award points either way on this question?
This means that Trump remains up 1.5 points on Clinton based on the above analyses.
Is there some other major point in addition to these others that it all boils down to, something that might swing the assessment toward Clinton? I think I have raised a good number of the most important ones that are on the minds of voters, especially the swing voters, and I can't really think of some point that Clinton would make up major ground on.
I'm not a big fan of Trump. I'm turned off by his crudeness, although he appears willing and able to learn. My focus here is on a comparison of these two flawed candidates on the basis of the balance of their strengths and weaknesses/shortcomings. I think the GOP could have put up a better candidate on the whole and such a candidate would have beaten out Clinton by better than 1.5 points. This is to say that despite all the hype from Democrats (whose penchant for larger government doesn't in any way indicate a superior moral or intellectual compass), about Clinton being the runaway enlightened choice, doesn't hold up under tough and fair scrutiny.
Perhaps Clinton would have some kind of advantage in having a former President as a key informal adviser. How much of an advantage one thinks this might be, is likely related to how much of a fan of the Clintons and the Clinton Machine, and of Democratic-progressive ideology, one is.
I would also point out how the candidates have been faring down the home stretch of the campaign. Clinton has studiously avoided serious contact with media for months, while Trump has not. Trump has greater stamina, does more events, wants it more, has more heart, and Clinton has been trying to run out the clock just as wikileaks and other scandals mount. Clinton has grown increasingly rhetorically deceptive in characterizing Trump as anti-woman, anti-minority, etc. I don't find that to be dignified or stateswoman-like. Clinton seems to think that her paint-by-numbers political career combined with purportedly superior ideology and moral compass entitles her to the position. She's somewhat complacent in a number of areas, and I don't respect or relate to that mindset. I think Democrats' fears about Trump are overblown or misplaced, their explanations for this or that Trump behavior being beaten out by better, simpler, less frantically partisan ones. They raise the fear of Trump, a "rude and crude" guy, having the nuclear codes. That's their last trump card so to speak. Why should we be particularly concerned in his case, based on our most objective assessment? Is he going to start a nuclear war? Putin and Kim Jung Un have nuclear codes, but haven't started nuclear wars. Is the fear that throwing Trump into the mix could easily increase the chances? That he's too easily provoked? I do see him being rather easily provoked into saying things (in a not-politically-finessed way) in response to insult or attack, but I'm more interested in what he would be provoked into doing, and I don't think Democrats know any more than anyone else does on that count. That we might not really know much in Trump's case is itself concerning. On the other hand, we do know for a fact that Clinton blatantly mishandled classified materials, exposing (via her unsecured server) national secrets to some 5 to 7 hostile actors. Should we trust this individual with the nuclear codes?
Partisans for either candidate tend to focus on a "worst-case scenario" involving the opposing candidate and a "best-case scenario" involving their own. I don't anticipate either of these in either candidate's case, nor do I play such biased games generally, so the best/worst-case scenario doesn't sway my view here either way. I do enjoy showing how a lot of these biased/partisan arguments tend to be self-defeating, e.g., with the "nuclear codes" card that the Democrats have been playing.
In closing, I don't claim to have covered all essential bases, or to have tied up all loose strands. I doubt that doing so would sway my tentative preference (which allows for some "margin of error") in a significant way. In any case, these sorts of things still stick in my mind: Trump's suggestion that a judge of Mexican heritage might not be objective in Trump's court cases; Hillary's statement in one of her highly-paid speeches that she could be of two minds - one public, one private - on any given issue presented before the American people; Trump up at 3am tweeting about accuser Alicia Machado and his more general pattern of attacking the source of criticism rather than the focusing on the criticism on its merits; the real levels of uncertainty about how Trump would govern; Clinton facing a mostly hostile Congress that would impede her "progressive" agenda; the general and more long-term state of the U.S. polity that led to this unappealing presidential choice (and for which the best medicine generally speaking is: philosophy, philosophy, philosophy, very preferably Aristotelian philosophy, that is, philosophy done best - but that is a topic left to another occasion).
[Addendum Nov. 6: In the interests of dialectical completeness: someone kindly notified me of this discussion between Sam Harris and Andrew Sullivan. Now, as bad as these two are at criticizing Ayn Rand's ideas, they - mainly Sullivan - make points that have made me reconsider, points the quality of which far exceed most of what I've been seeing from pundits and others during this election cycle - itself a distressing sign (either about my inability to find all the best arguments - the time constraints involved notwithstanding - or about the quality of the dialogue, or both...?). I do note, however, that "email scandal" was mentioned only once, in passing, during that entire talk. I think the 110 classified emails HRC routed through her private server is a big deal, certainly a bigger deal than Dem/HRC supporters have acknowledged - and they're certainly drinking a lot of Kool-Aid if they believe that an election victory over that other guy represents some kind of mandate for a Dem agenda. Anyway, yesterday I was leaning in the direction of marking the Trump oval on my ballot but now I'm probably going to leave the whole damn presidential section of the ballot unmarked. Sullivan is correct that electing Trump would be imprudent. The (less-imprudent but still deplorable) alternative is a lady who put her personal political ambitions above national security, which is certainly a good reason to reject any talk of a HRC/Dem mandate.]