Preheat the oven to 325°F (163°C). Grease and flour three 8x2 inch round pans.

In a medium bowl, whisk together the cake flour, baking powder, baking soda, and salt for about 30 seconds. Set aside.

Drain the crushed pineapple thoroughly using a strainer.

In another bowl, combine buttermilk, vegetable oil, drained crushed pineapple, and 1 tablespoon of vanilla extract. Set aside.

In the mixer, add softened butter and mix on medium speed until smooth. Gradually introduce sugar, mixing for 3-5 minutes until light and fluffy.

Add eggs one at a time, mixing until incorporated.

With the mixer on low speed, alternately add the flour and buttermilk mixtures, starting and ending with dry ingredients. Mix until combined.

Divide the batter evenly among the three prepared pans.

Bake for 28-30 minutes, until a toothpick comes out clean. Allow to cool for 10 minutes before transferring to a wire rack.

Freeze mixing bowl and beaters for 15 minutes. Whip heavy cream until stiff peaks form, keep refrigerated.

In another bowl, combine cream cheese, confectioners sugar, and 2 teaspoons of vanilla extract, beating until smooth. Fold this mixture into the whipped cream.

Reserve 2 cups for later, then mix the remaining frosting with the drained crushed pineapple.

Place the first cake layer on a plate. Brush the top with reserved pineapple juice.

Pipe a dam of frosting around the edges and fill with the pineapple whipped cream cheese filling.

Frost the exterior with a thin layer of whipped cream cheese frosting and chill for 15 minutes to firm up.

Apply a final coat of frosting, texturing as desired.

Decorate as desired, using additional pineapple filling or piping.