Interesting post, EnderD. There's a lot there and I will need to chew on it some before I can respond more thoroughly but here are a few thoughts off the top of my head.
While it is interesting to look at the etymology of the words masculine or feminine, I don't think we need to feel too strictly constrained by original meanings. Language evolves as society evolves. Our culture is not the same as it was centuries ago so it is no surprise that our language needs to change along with it to reflect new realities and new understandings.
I don't see masculine and feminine as highly precise words and they depend on cultural context (which is going to be frustrating to someone trying to come up with a concrete definition). They get us in the neighborhood but they aren't by themselves going to get us to the very doorstep of someone's identity.
Finally, labels that are truly limitless are also labels that are useless. If it can include anything then it tells us nothing.
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