Special equipment: a pastry bag fitted with a large round tip and a plastic straw
For the cupcakes: Preheat the oven to 350 degrees F. Line a 12-cup muffin tin with paper liners.
Sift the flour, granulated sugar, cocoa, baking soda and salt into a large bowl. Whisk together the buttermilk, oil, sour cream, food coloring, vinegar, vanilla and egg in another large bowl.
Add the buttermilk mixture to the flour mixture and stir until just incorporated. Divide the batter among the cupcake liners. Bake until a toothpick inserted in the center of a cupcake comes out with a few moist crumbs, 16 to 18 minutes. Remove the cupcakes from the tin and cool completely on a wire rack.
Microwave the chocolate and coconut oil together in a small microwave-safe bowl until mostly melted, about 1 minute. Stir, then microwave again until completely smooth, about 15 seconds more.
Use a small sharp knife to cut out and remove a plug from the middle of each cupcake, making sure not to go all the way to the bottom and leaving a 1/4-inch border around the side (eat the plugs). Brush the holes with the melted chocolate and place in the freezer until the chocolate hardens, about 15 minutes.
Whisk together the jam, 1 drop of red food coloring and 1 tablespoon water in a small bowl until completely smooth. Spoon 1 tablespoon of the jam into each of the chocolate holes; set aside.
For the cream cheese frosting: Meanwhile, beat the cream cheese in a large bowl with an electric mixer on medium speed until smooth and fluffy, about 2 minutes. Gradually beat in the butter until smooth. Add the confectioners' sugar and vanilla and beat until light and fluffy, about 1 minute. Scrape into a pastry bag fitted with a large round tip. Pipe on top of the cupcakes so the jam is covered.
Poke 2 holes into the frosting on each cupcake using the end of a plastic straw to resemble vampire bites, making sure you hit the cupcake and not the jam-filled hole. Drizzle the remaining jam into the holes to resemble blood.
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
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