Olive oil in the batter makes these better-for-you waffles extra crispy.
Preheat a Belgian-style waffle iron. Toss berries with 1/4 cup sugar, lightly mashing some with the back of a spoon.
In a large bowl, whisk together flour, baking powder, and salt. In another bowl, whisk together eggs, milk, oil, remaining 1/4 cup sugar, baking soda, and vanilla. Whisk wet ingredients into dry mixture just until combined.
Ladle 1 cup batter into waffle iron. Cook until golden and crisp, about 6 minutes. Repeat with remaining batter, whisking between batches for even cooking. Serve warm, with yogurt, macerated berries, and syrup.
Whisk a few teaspoons of water into the Greek yogurt for a light, smooth texture. Cut any leftover waffles into quarters and freeze them in resealable plastic bags; then reheat in the toaster.