Prepare the syrup. In a small saucepan, bring turbinado sugar, water, orange juice, orange zest, and cinnamon sticks to a boil. Stir constantly until sugar dissolves. Reduce heat, and simmer for 10 to 15 minutes. Remove from heat and cool completely. Syrup can be refrigerated in an airtight container up to 1 month.
Prepare the chicken. Preheat air fryer to 400°. In a shallow bowl, combine buttermilk, paprika, garlic powder, onion powder, salt, and pepper. In another shallow bowl, combine gluten-free flour, smoked paprika, salt, and pepper. Dip chicken in buttermilk mixture, then in flour mixture, patting to help coating adhere.
In batches, arrange chicken in a single layer in greased air-fryer basket; spray with vegetable oil. Cook until coating is golden brown and chicken is no longer pink, 7-8 minutes on each side or until the chicken reaches 165°F internal temperature. Preheat oven to 200°F. After each batch comes out of the air fryer, place inside the oven to keep warm.
Prepare the waffles. Preheat waffle maker. Whisk all wet ingredients together. Mix all dry ingredients together. Mix both mixtures until combined. To make the waffles, pour a small amount of batter in the center or the waffle maker and follow directions from your waffle maker.
Assemble the dish by adding a piece of chicken on top of a waffle. Drizzle with Turbinado syrup. Serve.