Preheat oven to 325 degrees F.
For cream cheese layer, in a small mixing bowl, combine 1?4 cup of the pumpkin, the cream cheese, maple syrup, 1 teaspoon of the pumpkin pie spice, 1 egg, and the vanilla. Beat with an electric mixer on medium speed until smooth. Spoon the cream cheese mixture evenly into the pie shells and smooth. Set aside.
For the pumpkin layer, in a large mixing bowl, combine the remaining pumpkin and the bourbon. Beat with an electric mixer on low speed until mixed. Add sweetened condensed milk, cinnamon, the remaining 2 eggs, and remaining pumpkin pie spice. Beat until smooth. Pour evenly over cream cheese layer to fill pie shells and smooth.
Place pies on a large baking sheet. Bake for 60 to 75 minutes or until set 1 inch from centers. Cool completely on wire racks. Drizzle with chocolate sauce.