Thank you OP for the theory, enjoyed contemplating it a lot.
I believe these cyberpunk stories are supposed to make us not trust anyone. I believe the missions leading up to the heist (Eve asking us to betray Dex, we can call Regina at one point to ask about Royce behind Dex's back etc...).
In this sense I think the game felt short in branching options, including the ability to lie. V can hardly lie. I mean, there are very few situations in which this is an option; in a world where everyone tries to play everyone else.
But what I think CDPR did to account for the lack of branching options (not just account for it. I believe this would happen anyway to a lesser degree on top of more branching options) was to leave a lot of open ending stories and put in place a lot of these misteries, related to characters or situations. So in my opinion the OP is playing the game (in this case the part of the game which isn't played on a controller or keyboard and mouse, but in the mind) but I don't think there is a definite answer. And Judy being a romanceable character I don't think there will ever be an answer to this one. But maybe other misteries will be resolved. I hope so because the high number of open ended stories makes them less remarkable for me. I remember in my first play through when there was a questline like the Peralezes' thinking it would end with a question mark. So it became expected.
