Masculinity The debate about what masculinity/femininity is, and what real men/women are, is often confused by people talking past each other.
Some derive masculinity/femininity from their view of how men/women are typically perceived, and some derive masculinity/femininity from how they think men/women should be. Both of these profiles are of course impacted by each other, but they are different nonetheless. From here on out, I will just talk about masculinity/men, since that is what your post is about, but my comment is general enough to apply to both men and women.
As for the former; before answering what is more or less masculine, one must first define what is typical of men. The most typical man would be a man who has the quantities of every trait in him that is average for men, in the eyes of the average human, right? No, that model does not take into account the synergies between the traits. Although x might be the average aggressivity of a man and although y is the most average happiness of a man, the most average combination of those two values may not be (x,y), since all these traits are not independent. So, not only is this practically very hard to quantify, it is even hard to quantify in principle.
Furthermore, who said the most average man would be regarded as the most typical man? Our perception of typicality is not a perfect representation of actual typicality.
Now, on top of the already complexity of defining what is perceived as typical for men, how does one derive what is the most manly from that? If most people perceive men as typically more disagreeable than most people, would that which we perceive as the manliest man be perceived as being as disagreeable as humanly possible? That which the perceived typical man has more/less of, the perceived manliest man has the most/least of? I do not buy that at all.
One can perhaps bite the bullet and say, actual masculinity does not perfectly align with perceived masculinity, but that doesn't fix the problem of quantifying masculinity. Some might try to get around the quantification issues by reducing it to some small number of independent factors that they purport are correlated with all the traits of masculinity (kind of like what psychometricians did with g and intelligence), but this would only worsen the disconnect between their supposed "masculinity" and perceived masculinity.
And yeah, then there's the discussion of what men ought to be, which is another doozie.
Personally, I leave it as this; I perceive people as more or less masculine and feminine, and I have intuitions about what men and women should be. These perceptions are mine and can be drastically different from other people's (especially those of different cultures). As for my deontic intuitions; I do not force them on anyone, nor do I place any weight on them. As a man, I do not find it morally important to behave as how my intuitions happen to tell me a man ought to behave; I do find it morally important to behave as how my intuitions tell me people should behave, however. I believe they're both instinctual, but at least the latter is less arbitrary.