For the cupcakes:
Preheat oven to 350 degrees F.
Line 28-30 muffin tins with cupcake liners and set aside
Sift together the flour, cocoa powder, baking powder, baking soda, and salt in a medium size bowl.
Add sugar and stir to mix.
Pour flour mixture into a large mixing bowl and add eggs, oil, milk and vanilla.
Beat on medium speed for 2 minutes, then stir in boiling hot water (consistency will be thin).
Fill cupcake liners 2/3 full with batter.
Bake for 20-25 minutes (oven temps can vary), or until a toothpick inserted into the center comes out clean. Cool completely while you make your frosting.
For the frosting:
Place butter into the bowl of a stand mixer and beat with whisk attachment until creamy.
Add one cup of powdered sugar and blend until smooth.
Add vanilla, milk and cream, then continue slowly adding sugar until all is incorporated and frosting is smooth and creamy.
Stir in chocolate chips and frost on cooled cupcakes.
*Store cupcake in a sealed container in the refrigerator until ready to serve