(Also see my reply to @theironfelix for the part about you guys commenting on all of the writer's stories. It really is great, and thank you.)
I love that my story has invoked these many theories. For most of my life I have never been much of a reader. for me it was always watching television growing up. It is where I saw most of my storytelling, rather than in a book. Many of my favorite shows (see my Twilight Zone portion of the other comment as well) told stories in a similar way that allow the viewer/reader to see different angles even though they are all watching/reading the same thing. To me those are the stories I usually enjoy the most, which I guess is why I write that way. I haven't written much to this point, but definitely see the pattern emerging. lol
Now your list of theories -
I did purposely leave it open to decide how Matt reacted after each restart. Did he let his heart win out and tell Sasha each time? Did he not say a word to her, but having this new knowledge was not able to cover up his nervousness to the point that Sasha, the trained spy picked up on it and had to protect herself once she felt something was off? Or perhaps, he told her about his encounter with Francis, forgives her and wants to help her get out of this mess, only to lead the agents in the corner to get spooked and start the shootout which kills Matt?
I love the other angles you come up with though. Each one could easily extend the story out in very different ways. I think in some way the purgatory angle was present in my mind, but the other three were not. The gaming one is especially intriguing. I definitely also like the angle where Sasha fell for Matt even though he was simply a means to her plans end, and now she is trying to bring him in so she doesn't lose him.
I am very happy you liked my story, and really do feel your comment actually makes the story better. It also makes me feel great knowing that it invoked these ideas from someone who writes much more than I do. Makes me think perhaps I have a chance at being good at this.