In a large bowl, combine the pancake mix, cocoa powder, sugar, vanilla and 4 cups water. Whisk until just combined -- a few small lumps left is just fine.
Heat a 10-inch skillet over medium heat. Add 1/2 teaspoon vegetable oil to the pan and swirl to coat evenly. Add about 2 cups of batter to the pan to make the first pancake. Cook for 6 minutes on the first side, adjusting the heat as needed to cook gently without burning. When small bubbles start to burst on the surface, sprinkle over a few chocolate chips and slide the pancake onto a flat plate. Place the pan over the plate and flip the pancake back into the pan. Cook for an additional 2 minutes, then remove the pancake to a wire cooling rack to cool completely. Continue with the remaining batter, going down by about 1/2 cup or 1/4 cup for each pancake. When the pancakes get small enough, feel free to simply flip with a spatula. You should end up with about 8 pancakes.
Place the cream cheese, butter, sugar, peppermint extract, salt and milk in a large bowl. Beat with a handheld mixer on medium speed until fully combined and light and fluffy, 3 minutes. Set aside.
Place the largest pancake on a flat cake stand. Spread some of the frosting over the top of the pancake, leaving a 1/3-inch border on the outside. Sprinkle with some of the crushed candy canes. Continue stacking the pancakes with the frosting and the candy canes, going down in size as you stack. Insert a long skewer through the center of the cake to hold the layers in place. Trim the skewer so that the top is flush with the top of the cake, and cover with more frosting. Decorate with mini meringue cookies on top if desired.
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