Preheat oven to 350 degrees F. Line a jumbo 6-cup muffin tin with paper liners (or a standard 12-cup muffin tin).
In a medium heatproof bowl, add the chocolate and cocoa powder. Pour the hot coffee over mixture and whisk mixture gently until smooth then set aside to cool. Let stand for 5 minutes.
In a small bowl, whisk together the flour, sugar, salt and baking soda and set aside.
Whisk sour cream, oil, eggs, vinegar and vanilla into the cooled chocolate mixture until smooth. Stir in the flour mixture until smooth.
Divide the batter evenly among the prepared muffins tins. Bake until the cupcakes are set and when inserted with a tooth pick it comes out clean, about 20-25 minutes (14-18 minutes for 12-cup muffins). Let cool slightly and then remove from pans and let cool completely.
Pipe with desired buttercream frosting and drizzle with chocolate ganache.
Buttercream frosting: In the bowl of a stand mixer, beat the butter until creamy and lightened in color. Add 1 cup of powdered sugar to the creamed butter and beat to combine, continue adding the powdered sugar 1-2 cups at a time until the mixture is light and fluffy, and add in extract and mix to combine.
Add in your raspberries and mix until raspberries have broken down and are fully incorporated into the mixture.
If the mixture is too stiff mix in 2-3 tablespoons of milk to reach desired consistency.
Add heavy cream to a small saucepan and bring to a boil. Put chocolate chips in a medium bowl and pour heavy cream over chips. Gently stir chocolate and cream together with a whisk until all of the chips are melted. Add butter and stir until all ingredients are fully combined and ganache is smooth and glossy.