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You could give it a shot if you hired an army of scouts and set them to specific leagues, focusing on quantity instead of quality.
The more times a player is seen, the higher his scouting report letter rating climbs. You'll want to get the best quality scouts you can, as well.
Worst case scenario - make a save at the point you need to make a decision, then make a copy of it so that you can go back to it if your decision doesn't work out.
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