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For anyone else curious about this, I finally got a chance to spray some water in the openings that I thought were unsafe for water to get into, and unsurprisingly, the water had no problem draining. Eventually all the water sprayed into these small openings drained at the bottom of the car.
TLDR -- don't worry if your windshield molding is not perfectly flush at the top corners, the water that gets under it will drain just fine.
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