Preheat the oven to 425 degrees F.
Gently roll out the chilled puff pastry on a lightly-floured surface until 1/4-inch thick. Transfer the dough to a parchment-paper-lined baking sheet and let relax in the refrigerator 10 minutes. Cut out 24 disks of puff pastry using a whiskey glass as a mold. Pierce the disks all over with a fork to prevent the puff pastry from rising too much during baking, and sprinkle the tops with sugar. Transfer the disks to the parchment-lined baking sheet (making sure they are not touching) and bake in the center of the oven, 10 minutes. Reduce the oven to 375 degrees F and continue baking until golden and crisp, another 5 to 10 minutes. Let cool.
For the pastry cream: Whisk together 1 cup of the raw sugar and the egg yolks in a bowl until pale yellow. Sift the flour directly over the egg mixture and whisk to combine. Combine the milk, vanilla seeds and pod in a small saucepot and bring just to a boil. Whisk the hot milk into the egg yolk mixture in a thin, steady stream, and then pour the contents of the bowl back into the saucepot, whisking continuously. Once the mixture starts to bubble, whisk vigorously 5 minutes. Remove from the heat, strain and separate the pastry cream into 3 equal portions. Place plastic wrap directly onto the surface of 1 portion of pastry cream and refrigerate to cool completely - this will be your vanilla pastry cream.
Stir the melted chocolate into a second portion of pastry cream until completely incorporated. Cover the surface directly with plastic wrap and refrigerate.
Combine the raspberries, remaining 1/2 cup sugar and the lemon juice in a small saucepot and cook until the raspberries begin to break down and release their juices, about 5 minutes. Puree in a blender, and then allow to cool before adding directly to the last portion of pastry cream. Cover the surface directly with plastic wrap and refrigerate.
Whip 1 cup of the cream into firm peaks, and then add half to the cooled chocolate pastry cream and whisk well to combine. Whisk the other half of the whipped cream into the cooled vanilla pastry cream to combine.
Whisk together the icing sugar and remaining 2 tablespoons cream in a small bowl. If the icing is too thick, add more cream until you get the right consistency.
Line up 8 whiskey glasses. Place 1 puff pastry disk at the bottom of each glass, and spoon 2 heaping tablespoons of the pastry cream flavor of your choosing on top. Place another puff pastry disk on top of the cream, followed by another layer of pastry cream. Spread the icing over the top of 8 disks, and drizzle with melted chocolate. Finish each glass with an iced top, and then chill and serve immediately or within a few hours.