Preheat oven to 350 Degrees F. Combine wafers, pecans and melted butter in a bowl. Press into bottom of a 12-inch springform pan. In food processor fitted with metal blade, mix cream cheese until smooth. Add brown sugar and process until blended. Add eggs one at a time, processing until fully incorporated, then blend in heavy cream. Add flour, salt, cinnamon and 1 teaspoon vanilla and blend until smooth. Add pumpkin and blend until smooth.
Pour filling over crust in pan. Bake for 1 hour and 15 minutes. Remove from oven. Use a knife to loosen cake from side of pan. Let cool completely before slicing.
Meanwhile, make toppings. Combine whipped cream and bourbon in a bowl and mix until blended. For chocolate sauce, combine half-and-half and butter in a sauce pan over medium heat. Add chocolate chips and 1/4 teaspoon vanilla and stir until chocolate melts and mixture is smooth. Remove from heat and cool.
Remove side of springform pan and slice cheesecake. Top each piece with a drizzle of chocolate sauce and some bourbon whipped cream.