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In a medium bowl, combine cream cheese, powdered sugar, and vanilla and stir until blended. Spread cream cheese mixture on one tortilla and sandwich with remaining tortilla. In a large skillet over medium heat, melt 1 tablespoon butter. Add quesadilla and cook until golden on one side, about 3 minutes. Flip and cook until second side is golden. (Add second tablespoon of butter if skillet is dry.) Sprinkle with cinnamon sugar, top with strawberries, and drizzle with melted chocolate.