Your hypothetical doesn't follow because in God's design it is always a one-time run through otherwise it would be a bizarre form of Hinduism. If it is not a one time run through then you take that same soul and run them through it again which violates the law of man made in God's image. Your hypothetical violates said premise.
Craig has some strange notions that do not follow logically which stem from his works based salvation as one would expect.
And libertarian free will is not true free will since all of our choices are within God's divine providence.
The original Molinism was by a non-OSASer like Craig, both unsaved going to Hell. What I do is apply the principle of middle knowledge to OSAS Arminian, however I am aware of the limitations of Molinism so don't expect much from it. It always leaves you wanting anyhow so it is not the ultimate answer of how God reconciles His infinite foreknowledge with free will.
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