Preheat oven to 350 deg F. Divide ¼ c butter between two 9” round cake pans and place in oven until butter is melted. Remove from oven and spread the melted butter around the bottoms of the pan to make sure they’re evenly coated. Sprinkle the muscovado sugar, ⅔ c per pan, over the butter evenly. Place 5 pineapple rings around the the pan, on top of the muscovado sugar, and place one smaller ring in the middle. Place one maraschino cherry in the center of each ring and fill the spaces between the pineapple rings on the outer edges with diced pineapple, about 1 tablespoon each space. Set the remaining pineapple aside for adding to the cake batter.

In a medium bowl whisk together the flour, baking powder and salt. Set aside

In the bowl of a stand mixer add the butter and beat until fluffy, about 30 seconds. Add the sugar and beat again until soft and fluffy, scrape downs the sides of the bowl with a spatula when needed. Add the eggs in one at a time, beating well after each addition. Then add in the rum and the diced pineapple and mix for another 30 seconds. Scrape down the sides of the bowl again.

Slowly add in the flour mixture alternating with the buttermilk in several additions, mixing on low a few turns in between additions. Once all is combined mix on medium about 30 seconds. Divide the batter evenly amongst the cake pans and bake for 40-50 min or until a toothpick comes out clean.

Cool the cakes for about 10 min. Carefully loosen the edges with a knife then invert using a cooling rack and cool completely. Have the cooling rack placed on a foil covered pan to catch any drips. Remove the pan and scrape any remaining bits off the pan and spread on the cake. Refrigerate at least 6 hours to overnight, well wrapped in plastic wrap

Place all in a saucepan on the stove and turn heat to medium, stirring until sugar is dissolved. Raise heat and bring to a boil, once boiling lower the heat and simmer 20-40 min mashing the diced pineapple occasionally. Once the syrup is thickened strain into a jar and keep refrigerated. Keeps well about 2 weeks well chilled in a covered container such as a mason jar. This syrup is also great for cocktails, pancakes and waffles.

Heat the oven to 475 degrees

Wrap aluminum foil around the bottom of a greased, 9-inch spring form pan (to prevent leakage from the water bath).

Place the spring form pan in a large roasting pan, for the water bath

In a large bowl, beat the Neufchatel cheese with an electric mixer on low speed.

Gradually beat in the sugar, eggs, greek yogurt, flour, vanilla and pineapple syrup.

When mixture is blended, scrape down the sides, and pour it into the spring form pan.

Pour hot water in the roasting pan filling so it reaches about halfway up the outer sides of the spring form pan being careful not to get any water in the cheesecake.

Swirl in maraschino cherry juice and crushed pineapple, making sure the juice reaches the sides and bottom, add more if desired.

Place the pan in the oven, being careful not to spill the water out of the pan or into the spring form pan.

After 10 minutes, reduce heat to 350 and bake for another 50-75 minutes until the top is set.

Remove from oven and carefully take the pan out of the waterbath and let cool ten minutes. Place in the refrigerator still in pan and cool completely. If using to layer with the cake immediately, carefully remove from the spring form pan, using a thin long knife run around the underside and remove from the base to set on top of the bottom layer of the cake. If not using immediately wrap in plastic wrap and seal in an airtight baggie and freeze. Thaw slightly before using.

Whip the chilled whipping cream to soft peaks. Add in the powdered sugar and vanilla in and whip again until stiff peaks are formed. Keep chilled.

Place one of the pineapple upside down cakes on a cake plate with the pineapple rings facing up. Spread a thin layer of whipped cream and then place the cheesecake on top. Spread another thin layer of whipped cream and place the other pineapple upside down cake on top. Frost the sides with whipped cream and pipe swirls on top. Place a maraschino cherry in each swirl. Keep Chilled until ready to serve.