Preheat the oven to 325 degrees F and spray a 9-by-5-inch loaf pan with cooking spray.
Cream the butter and sugar together in the bowl of an electric mixer fitted with the paddle attachment on medium speed until light and fluffy, 4 to 5 minutes. Add the eggs, one at a time, beating well after each addition.
Mash the bananas in a small bowl (you should have about 1 cup), then add to the mixing bowl and beat until just combined. Turn the mixer to low and slowly add the flour, milk, baking powder, baking soda, cinnamon and salt and beat until just combined.
Pour the batter into the prepared loaf pan and bake until a toothpick inserted in the center comes out clean, about 1 hour and 10 minutes. Let cool on a rack for 15 minutes, then invert the bread onto the rack to cool completely, about 1 hour. Slice the dark crispy edges off all 4 sides of the bread.
Line a baking sheet with parchment paper. Crumble the bread into very small pieces in a large bowl. Add the frosting and mix with a spoon until the bread is a creamy consistency that can be rolled into a ball without crumbling. Roll the banana bread mixture into heaping teaspoon-sized balls with your hands (about 1/2 ounce each) and place them on the lined baking sheet. Chill the truffles in the refrigerator until cold, about 2 hours and up to overnight.
Put the chocolate chips and oil in a medium microwave-safe bowl and microwave in 30-second intervals, stirring between each, until melted, about 2 minutes.
Toss the truffles, one at a time, in the chocolate mixture until completely coated. Use a fork to remove the truffles from the bowl and return to the lined baking sheet. Sprinkle with the topping of your choice (if drizzling with caramel sauce or extra melted chocolate, let the truffles harden first). Repeat with the remaining truffles, reheating the chocolate in the microwave in 30-second intervals if beginning to harden. Chill the truffles in the refrigerator until the chocolate is hardened, about 10 minutes.
When measuring flour, we spoon it into a dry measuring cup and level off the excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
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