You're demanding that I reduce my answer to a simple yes or no because you have a response tucked up your sleeve, so there's two things I can do. I can provide you with the answer you're looking for, wait to hear what your response is going to be and then spend a bunch of time explaining to you that it's more complicated than that. Or, I can just leave you with the more comprehensive answer that I've already given. Wow, what a decision.
When we're talking about complex philosophical considerations, yes or no answers just don't cut it because it's often critical that you consider an idea within a particular context or as part of a larger framework of reasoning which is impossible to present with a single word.
With that in mind, I shall reiterate a little. God had a plan, and there were certain things that needed to happen in order for it to be realized. But because this plan included the creation of a universe within which some or all events were not predictable with 100% accuracy, God needed to intercede at certain critical points throughout history to keep things on track. So did God know how things were going to turn out? No, not exactly. But He
was in a position to ensure that the overall outcome was what He wanted it to be. So the answer is yes
and no, depending upon the kind of question you're asking, which whether you realize it or not, isn't clear.
Yes, He knew how His overall relationship with man was going to turn out both because He understood man and because He interceded at critical points to keep things heading in the desired direction. Remember, we're not talking about
quantum mechanical principles* here where a single interaction on God's part would collapse the
wave function* of free will. He can intercede without compromising the fundamental nature of the reality that He created.
No. God could not be certain what any individual in particular would choose to do, and if the universe is fundamentally probabilistic in nature, even if the classically deterministic world that
we seem to live in is only jolted occasionally by a random quantum event (some neuroscientists have suggested that you might be able to reconcile free will with what appears to be a classically deterministic brain by considering this idea) then neither did God know precisely how the physical universe was going to unfold. Certainly not every detail, anyway. In case it occurs to you however, the free will of a human being has nothing to do with, for example, God interceding to prevent a huge asteroid destroying the planet and subsequently ruining His plans.
*Please forgive my borrowing of terms here. It's just an analogy. I'm not a quantum quack, I promise you