Berries: Melt dark chocolate, dip strawberries, and let dry. Melt white chocolate, tint pink, and drizzle over berries. Chill.
Batter: Whisk dry ingredients. Mix in egg, milk, oil, and vanilla. Stir in hot water.
Bake: Fill liners halfway and bake at 300°F for 18–23 minutes. Cool completely.
Frosting: Puree and strain strawberries. Beat butter and shortening. Add half the sugar, 2 tbsp puree, and then remaining sugar. Adjust consistency with extra puree.
Assemble: Pipe frosting onto cupcakes and top each with a chocolate strawberry.