Make the waffle batter: Whisk the flour, confectioners' sugar, cocoa powder, baking powder, baking soda and salt in a large bowl. Whisk the milk, melted butter and coconut oil, egg yolks and vanilla in a medium bowl until combined. Add the milk mixture to the flour mixture and stir with a rubber spatula until combined (it's OK if a few lumps remain).
In a separate large bowl, whisk the egg whites until stiff peaks form, about 3 minutes. Fold the beaten egg whites into the batter, then fold in the mini chocolate chips. Loosely cover with plastic wrap and let stand at room temperature at least 15 minutes and up to 1 hour.
Meanwhile, make the cherry sauce: Bring the cherries and their juice, preserves and maple syrup to a simmer in a medium saucepan over medium-high heat. Cook, stirring occasionally, until syrupy, about 20 minutes. Remove from the heat and stir in the almond extract. Set aside until ready to serve.
Cook the waffles: Preheat the oven to 200 degrees F. Set a wire rack on a baking sheet. Preheat a waffle iron (preferable Belgian-style). Lightly brush the waffle iron with melted butter; pour in the batter, filling each compartment about three-quarters full. Close and cook according to the manufacturer's instructions. Transfer the waffles to the rack and keep warm in the oven. Repeat to make more waffles, brushing the waffle iron with more butter each time.
Thin the cherry sauce with a splash of water, if necessary. Serve the waffles with whipped cream and the sauce.