For the chicken: Fold together the chicken tenders, buttermilk, tarragon, thyme and cayenne pepper in a shallow dish until thoroughly combined. Cover and refrigerate overnight.
Remove the chicken and buttermilk mixture from the refrigerator. Sift 1 cup flour, garlic powder, 2 teaspoons salt, 1 teaspoon pepper and onion powder into a separate shallow dish.
Preheat the 3 cups oil in a large cast-iron pan over medium-high heat to about 350°F. Thread each tender onto a skewer.
Dredge each skewered tender in the flour mixture, coating completely and shaking off any excess. Dip each back in the buttermilk mixture and again in the flour mixture, gently shaking off any excess.
In small batches, gently drop the skewers into the oil and fry, about 5 minutes. Flip and fry until golden brown, an additional 3 to 5 minutes. Drain on paper towels and season with salt and pepper.
For the waffle batter: Place the 2 1/4 cup flour, milk, 1 1/4 cup and 2 tablespoons oil, sugar, vanilla extract, baking powder, baking soda, salt and eggs in a large bowl and whisk until no lumps remain. Dip the fried tenders in the batter, coating completely. In batches, gently drop the skewers back into the oil and fry, about 4 minutes. Flip and fry an additional 3 to 4 minutes. Drain on paper towels.
Just before serving, brush with a light coating of melted butter and drizzle with maple syrup. Serve warm.