Place the chicken pieces in a large plastic Ziploc bag and cover with the buttermilk. Seal bag and refrigerate for at least 4 hours. This will help to tenderize the chicken.
Remove chicken from bag and pat dry with paper towels. Set aside.
In a large cast iron skillet, heat about 1 cup of vegetable shortening. You want to get about an inch or so layer once it's melted (or at least be able to cover the chicken pieces by half). Heat until between 325 - 375 F.
In a medium shallow dish, combine the flour, cornstarch, cayenne pepper, garlic powder, onion powder, and Italian seasoning.
Dredge each piece of chicken in the flour mixture and shake off any excess.
Working in batches (I did about 4-5 pieces per batch), fry the chicken until cooked throughout, about 4-7 minutes per side (depending on the type of pieces you used, some cook faster than others).
While the chicken is frying, you can prepare your waffles.
In a medium bowl, combine flour, baking powder, salt, and sugar. In a small bowl, whisk together the egg, milk, and vanilla until combined. Combine the dry ingredients with the wet ingredients. Then whisk in the melted butter until just incorporated.
Grease your waffle maker with non-stick spray or butter and add about 1/2 cup of batter per waffle. Cook per machine instructions and waffles are browned and crisp.
Serve fried chicken atop one large waffle and drizzle maple syrup around waffle. Enjoy absolute bliss.