I don't think the side flashes are about them IF they didn't crash, it's more than that. They keep running into each other and having weird moments, and the appendix thing. Jack couldn't remember, as if he knew it wasn't what he thought, but wasn't totally clear.
I think Julliet saying, "it worked" to Miles, means more than people are giving it credit for. Perhaps it did actually work, and they are off the island, and the memories are just goofed up along with time. Somehow it will all meld together, who knows?
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