Make the cake: Preheat the oven to 350°F. Prepare two 6" cake pans by greasing with butter/baking spray and lining with parchment paper.
Using a food processor or blender, finely chop the dried cherries with 1/4 cup of the sugar.
Beat the butter and remaining sugar until the mixture lightens in color and texture, ~90 seconds. Add the oil, and beat until the mixture is light, ~60 seconds.
Beat in the sugar/cherries, salt, baking powder, baking soda, almond extract, and cherry juice concentrate.
Beat in the eggs one at a time, scraping the bowl after each addition. Gently beat in the flour, alternating it with the milk.
Divide the batter between the cake pans and bake for 16 to 18 minutes, until cakes are light brown and a toothpick from the center comes out clean.
Make the frosting: Place a completely clean bowl from your stand mixer over a saucepan filled with simmering water ensuring that the bowl doesn't touch the water.
Add the egg whites and sugar to the bowl, whisking constantly but gently, until temperature reaches 140°F, or until the sugar has completely dissolved and the egg whites are hot.
Attach the bowl to the mixer fitted with the whisk attachment and begin to whip until the meringue is thick, glossy, and the bottom of the bowl no longer feels warm, about 7 to 10 minutes.
Switch over to paddle attachment and, with mixer on low speed, add the butter cubes, one at a time, until incorporated. Continue beating until it has reached a silky smooth texture. Add the vanilla, salt, and chocolate continuing to beat on low speed until well combined.