Prepare the waffles: Heat olive oil in a medium skillet over medium-high. Add corn, and cook, stirring often, until tender, about 7 minutes. Remove from heat, and cool completely.
Process milk and 1/2 cup cooked corn kernels in a blender until smooth, about 30 seconds. Set aside.
Preheat oven to 220°F. Whisk together flour, baking powder, salt, and baking soda in a medium bowl. Whisk together milk-corn mixture, butter, and eggs in a small bowl, and stir into flour mixture with remaining 1/2 cup cooked corn kernels until combined. Cook batter (about 1/2 cup per waffle) in a preheated, lightly greased waffle iron until golden brown, 4 to 5 minutes. Place waffles on a wire rack set on a baking sheet, and keep warm in preheated oven.
Prepare the lobster: Remove shell completely around lobster tail meat, leaving fins on. Pour canola oil to a depth of 1 1/2 inches in a small Dutch oven; heat oil over medium to 325°F. Stir together flour, salt, and both peppers in a medium bowl. Dip lobster tails in beaten eggs; dredge in flour mixture, shaking off any excess. Cook in hot oil until golden brown and crispy, 2 to 2 1/2 minutes per side. Place 1 fried lobster tail on each waffle, and serve with Spicy Maple Syrup.