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Preheat oven to 325° F, then heavily grease and flour two 9-inch round cake pans.
In the bowl of a stand mixer with the paddle attachment, cream the butter and sugar until light and fluffy.
Add the eggs, vanilla, and oil and beat until well combined.
In a separate medium bowl, sift the flour, baking powder, and salt.
Gradually add the dry ingredients into the mixing bowl on low speed until the flour is just combined.
Add the milk and mix until the batter is smooth.
Using a spoon or rubber spatula, stir in the maraschino cherries.
Evenly distribute the batter into the two pans and bake for 25 to 30 minutes, or until a toothpick comes out clean.
Remove the cakes from the oven and let them cool completely, then flip each onto a cooling rack.
At this point, either slice each cake in half horizontally to make a four-layer cake, or let it remain a two-layer cake.
While the cake cools, make the frosting.
In the bowl of a stand mixer with the whisk attachment, add all the ingredients and whisk until light and fluffy, about 8 minutes.
Frost the cake as desired and garnish with fresh cherries.