Preheat the oven to 425 degrees F with a rack set in the top. Place a baking sheet on the rack to heat up.
Whisk together 1 cup of the maple syrup and the chipotles in a bowl. Season with salt.
Place the chicken drumsticks and thighs in a large bowl and sprinkle liberally with salt and pepper. Add half of the melted butter and toss the chicken to coat. Remove the hot baking sheet from the oven and carefully place the chicken on the baking sheet, skin-side up for the thighs. Bake until the skin is golden brown and crispy and the internal temperature on an instant-read thermometer registers 160 degrees F, 20 to 25 minutes.
Meanwhile, make the waffles. Preheat a 6 1/2-inch waffle iron to medium-high heat. Whisk together the flour, grits, baking powder and 1/4 teaspoon salt in a mixing bowl. In a separate bowl, whisk together the milk, egg and the remaining melted butter and maple syrup. Slowly mix the wet ingredients into the dry ingredients, stirring until just combined.
Spray the hot waffle iron with the cooking spray. Pour 1/2 cup of the batter in the center of the waffle iron, close the lid and cook until golden brown and cooked through, 3 to 5 minutes. Transfer the cooked waffle to a plate. Continue cooking waffles with the remaining batter, spraying between batches, making 4 waffles total.
To serve, place a waffle on a large plate. Top each waffle with a drumstick and thigh. Drizzle all over with the chipotle maple syrup, serving any remaining syrup on the side.