What would it take to get a Roman Empress?

Well you'd probably have to start quite early, while Roman women were afforded great legal protection for it's time it was still patriarchal like all civilizations back then. Maybe something like a successful monarchy that is established, while that would be still slanted against women it is more likely for empresses to come from the limited pool of royal children than the non-existent female aristocracy/military. (more than the usual flukes where male emperors die and female relations take over)

I'm not sure when but the latest is before the 3rd century when everything went to hell and Diocletian reduced individual liberties by militarizing Roman society.
 
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