Brush insides of waffle bowls with maple syrup. Working one at a time, invert waffle bowl onto a microwave-safe plate and cover with a damp paper towel. Heat in microwave 30 seconds; waffle will soften and flatten. Immediately mold waffle into a hard taco shell shape with your hands. Let rest until set, about 2 minutes.
Carefully fill waffles with ice cream (about 6 Tbsp. per taco); smooth surface with the back of a spoon or offset spatula. Transfer to a plate or parchment-lined rimmed baking sheet and freeze until firm, at least 1 hour.
Combine chocolate and oil in a small, microwave-safe bowl. Heat in microwave in 30-second intervals until melted and smooth, stirring occasionally. Stir in peanuts.
Working one at a time, roll ice cream side of taco into melted chocolate to completely cover ice cream. Return tacos to plate and freeze again until chocolate is set, about 10 minutes.
Tacos can be frozen in an airtight container for up to 7 days.