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Whisk oats, almond milk, yogurt, peanut butter, 2 tablespoons chocolate chips and vanilla together in a large bowl until combined. Refrigerate, uncovered, until set and slightly thickened, about 30 minutes.
Meanwhile, stir the remaining 3 tablespoons chocolate chips and coconut oil together in a small microwave-safe bowl. Microwave on High for 45 to 60 seconds; stir until the chocolate chips are completely melted and incorporated into the oil.
Divide the oat mixture among 4 (8-ounce) jars, about 1 cup each. Spoon about 2 teaspoons of the melted chocolate chip mixture over each jar, tilting to cover the entire surface. Refrigerate, uncovered, until the chocolate layer is just set, about 10 minutes. Sprinkle with flaky salt; cover and refrigerate until the oatmeal has thickened and the chocolate layer is fully set, at least 12 hours or up to 4 days.