Preheat oven to 450F. Top a baking sheet with a wire rack and set aside.
In a small bowl combine milk and vinegar. Stir and set aside.
In another small bowl add flour, corn meal, paprika, ancho chile, salt, pepper, red pepper flakes and cayenne. Whisk ingredients until evenly distributed.
Slice tomatoes ¼-inch thick. One slice at a time, dip tomato in curdled milk, dip in flour, dip again in curdled milk and repeat in flour ensuring that the slice is evenly covered. Tap slice on side of bowl to remove any excess.
Place the coated tomatoes on the rack. Drizzle the tops of the tomatoes with olive oil and transfer to oven.
Bake tomatoes 10 minutes, flip, and cook for 20 minutes more.