Preheat oven to 350 degrees. Grease 2 9 inch cake pans with butter or oil.
Sift the freeze dried strawberry powder with the sugar. In a large bowl, cream the butter and strawberry sugar until fluffy, about 3-4 minutes. Beat in the eggs, one at a time, until fully incorporated. Whip in the vanilla, Greek yogurt, and dye if using. Add the flour, baking powder, baking soda, and salt. With the mixer running, slowly stream in the wine. Do not overmix.
Divide the batter evenly between the cake pans. Bake 30-35 minutes until the center is set and an inserted toothpick emerges with just a few moist crumbs. Let cool in the pans for 10 minutes, then run a knife around the edges to release the layers and flip onto a wire rack. Cool completely.
When the cakes are cooled, make the frosting. In a bowl, whip the butter and vanilla on low speed until combined. Add in 4 cups of powdered sugar and 1/3 cup cream and mix to combine, then increase the speed to medium high and whip until very light and fluffy. If needed, pour in more sugar 1 tablespoon at a time until the frosting is soft and spreadable.
Scoop out 1 1/2 cups of the frosting. Mix with red dye until you reach a vivid, strawberry-esque hue.
Place one cake layer on a flat plate or cake stand. Frost the top generously, then add the second layer. Frost all the way around the cake until completely covered. Using a flat, small frosting tip, pipe on strawberries all around the cake. They don't have to be perfect!