Preheat the oven to 335F/168C. Prepare a large Bundt cake pan by spraying the pan well with a baking spray; or use the butter and flour method.
In a large mixing bowl, cream together the softened butter, sugar and vanilla for a few minutes until the mixture is fluffy. Add in the melted chocolate and mix again until smooth. Begin adding the eggs, one at a time, and mix well after each addition. Warm the milk in the microwave until lukewarm, then pour into the batter.
In a separate bowl, combine the dry ingredients: flour, salt and baking powder. Sift the dry ingredients into the batter and mix for 30 seconds with a hand mixer, or mix in by hand just until the dry ingredients are incorporated.
Drain as much of the juice from the crushed pineapple as possible, then add to the batter and fold. Transfer the batter into the prepared pan. Bake in the preheated oven for 1 hour, up to 1 hour and 20 minutes; until a toothpick inserted into the center comes out clean.
Allow the cake to cool upright in the pan for about 15 minutes, then invert onto a cooling rack to cool completely.
Cake can be enjoyed with or without frosting. For the whipped cream, simply combine the chilled heavy cream, sugar, vanilla and salt in a stand mixer bowl. Whisk on medium-high speed until stiff peaks form, about 5 minutes.
If desired, transfer the cream into a piping bag and garnish the top of the cooled cake. I used a French open star tip #8ft.
Un-frosted cake can stand at room temperature, covered with plastic. Refrigerate frosted cake in a covered stand.