I don't think there's a way to sync up the dropdown on the Loot window and reference the guild window's member view, at least not directly from the UI hierarchy.
I didn't read through your questions/idea to the fullest exent, but probably a best bet way to do something like easier DKP assignment from the loot window, would be to figure out what the slash commands are for assigning DKP and see if it uses any kind of normalized strings. My guess is probably: No, and it uses IDs that change depending on the guild member list, or simply based on the highlighted member.
Could use manually select a guild member row, and do something with the loot window? I suppose, but then you're already manually selecting a member so why the extra steps?
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