Great stuff! You really know how to break it down. You've put into focus all of the things I've been tinkering with in my head but just didn't have any perspective on.
I think the reason why I want to explore Shadowrun again using AW is to focus on the psychological trauma of having, in a period of less than half a century, cybertechnology AND magic becoming solid features in our world. Having said that, the loss of Essence by gaining cyberware isn't a huge deal thematically (like you become a colder, deader person or whatever), unless it's affecting a magical character since Essence is the connection to magic. That goes into the magic system of SR, where some spells target a character's Essence (i.e. a healing spell is harder to cast on a low-Essence character). For me I suppose it's a pretty mechanical feature overall.
Let me try to answer your question of what do I want Essence to do in my game.
"Essence will power the magical abilities of awakened characters and indicate the metaphysical wholeness of characters, both awakened and mundane."
So I guess three things:
• power magical moves
• gauge how much chrome a body can handle
• indicate how susceptible to magic a body is
I wouldn't bother with both Magic and Essence.
I was already on to this. For this type of hack, I see the moves as ways to cover the different skills from SR. So there will be conjuring, sorcery, etc moves, all based on the intrinsic power (Essence) of the character. And then Initiation will be a move that can be taken after the character takes a certain number of other advances.
Essence and Synth might either always sum to 1, or perhaps the combined totals could never exceed 1. So if one is +2 the other is -1, if one is +1, the other is zero.
I like this a lot, I was just having trouble with the balance. But then it changes what Synth means. In The Sprawl, it represents your ability to control and be at one with the chrome, right? In Shadowhack, would Synth go up when you gain cyberware? If a non-cybered character gets a piece of cyberware, his Essence goes down but does his Synth go up? And then, if he gets another, and it goes up again, does that represent not only that he has more cyberware, but that the more he has, the more he knows how to use all of it? I think I'm cool with that. It's just another sort of "wholeness" I suppose.
By the way, I love the hunted/owned/unreliable cyberware stuff you did. It makes the whole thing so much more scary and intense.