@ChrisDizon This is exactly the issue I have posted about in another thread trying to bring it to the attention of the Sketchup Team.
You should be able to use intersect faces with model to create the edge for you. It works with solid tools and with raw geometry but not Intersect with Model. As you can see in my gif if you make the face pass through another face it works , but not when the faces are planar.
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