Preheat your oven to 350°F (175°C). In a medium bowl, combine the cookie crumbs and ¼ cup granulated sugar. Pour in the melted butter and mix until well combined. Press the mixture firmly into the bottom of a 9-inch springform pan. Bake for 8-10 minutes, or until lightly golden. Remove from oven and let cool while you prepare the filling.

Reduce oven temperature to 325°F (160°C). In a large bowl, using an electric mixer, beat the softened cream cheese until smooth and creamy. Gradually add 1 cup granulated sugar, beating until well combined. Beat in the eggs one at a time, mixing just until incorporated after each addition. Stir in the vanilla extract and ¼ cup heavy cream until the mixture is smooth. Be careful not to overmix, as this can introduce too much air and cause cracks.

Pour the cheesecake filling over the cooled crust in the springform pan. Place the springform pan in a larger roasting pan. Pour hot water into the roasting pan, reaching about halfway up the sides of the springform pan (this is a water bath, which helps prevent cracks). Carefully transfer to the preheated oven and bake for 50-60 minutes, or until the edges are set but the center still jiggles slightly when gently shaken. Turn off the oven, crack the door open, and let the cheesecake cool in the oven for 1 hour. Remove from oven, remove from water bath, and let cool completely on a wire rack. Once cool, refrigerate for at least 4 hours, or preferably overnight, before adding toppings.

In a heavy-bottomed saucepan, combine 1 cup granulated sugar and ¼ cup water. Cook over medium heat, stirring until the sugar dissolves. Once dissolved, stop stirring and allow the mixture to boil until it turns a deep amber color. This can take 8-12 minutes. Watch carefully as it can burn quickly. Once the desired color is reached, immediately remove from heat. Carefully and slowly whisk in the warmed heavy cream (be very careful, as the mixture will bubble up vigorously). Stir in the butter, vanilla extract, and pinch of salt until smooth. Let the caramel cool slightly before using.

Preheat oven to 300°F (150°C). Spread the shredded sweetened coconut in a single layer on a baking sheet. Toast in the oven for 5-10 minutes, stirring occasionally, until golden brown and fragrant. Watch carefully to prevent burning. Let cool completely.

Once the cheesecake is thoroughly chilled, carefully remove it from the springform pan. Spread a generous layer of the cooled caramel topping over the top of the cheesecake. Sprinkle the toasted coconut evenly over the caramel. For the chocolate drizzle, melt the semi-sweet chocolate chips with coconut oil in a microwave-safe bowl in 30-second intervals, stirring until smooth. Drizzle the melted chocolate over the cheesecake in a zigzag pattern, mimicking the Samoa cookie design. Refrigerate for another 30 minutes to allow the toppings to set.