Flux,
I think your points on living longer and women being more free now to choose are excellent insights into the question of why baldness hasn't been bred out of humanity.
Still, though, I see bald men with women. Not to mention fat men with women, dwarf men with women and even impotent men with women who are willing to forego children.
I'm sure these women who date/marry/screw bald men are the same ones who joke about about bald men. However, even though they count baldness as a "con", they still find a reason to interact with baldies. So I suppose in that respect, they're no different than men who pant after women on the cover of Maxim, but still go home to their homely wives/girlfriends at the end of the day.
I don't think there's any benefit or detriment to balding. It's just one of those variations, like ear size, height, intelligence, or eye color.
I just wish we glorified hairloss instead of a full, youthful head of hair.
O.