Grease a waffle iron with cooking spray and preheat according to manufacturer's instructions.
Whisk flour, sugar, baking powder, and 1/2 teaspoon salt together in a large bowl.
Whisk milk, beaten eggs, butter, and vanilla extract together in a separate bowl. Pour over flour mixture; stir until batter is just moistened.
Scoop 2 teaspoons of batter into the waffle iron for each waffle pop, leaving space between each one. Insert a lollipop stick 3/4 of the way into each pool of batter. Close lid; cook until golden and crispy, about 1 minute. Transfer waffle pop to a cooling rack. Repeat with remaining batter and lollipop sticks.
Melt dark chocolate in a microwave-safe glass or ceramic bowl in 15-second intervals, stirring after each interval, 1 to 3 minutes.
Scoop melted chocolate into a pastry bag fitted with a small writing tip or into a plastic resealable bag with a corner snipped off. Drizzle chocolate over one side of the waffle pops.
Sprinkle peanuts and a small pinch of flaked salt over pops while chocolate is still warm. Let cool until chocolate firms up, about 5 minutes.
All waffle irons are built differently and will affect the batch size. My circular waffle iron was able to close over waffle pops baked in the 2 front sections only, so I was able to make 2 at a time. Your batch size may vary.
Per Serving: 70 calories;4 g fat;
7.8 g carbohydrates;
1.5 g protein;
14 mg cholesterol;
143 mg sodium.