Beat cream cheese, pumpkin pie spice and 1/4 cup of the sugar in large bowl with electric mixer on medium speed until smooth and creamy. Add coconut milk; beat until well blended.
Beat cream and remaining 1/4 cup sugar in another large bowl with electric mixer on medium speed until stiff peaks form. Add 1/2 of the whipped cream to cream cheese mixture; stir until well blended. Gently stir in remaining whipped cream.
Mix crushed cookies, macadamia nuts and coconut in medium bowl. Spoon 1 tablespoon cookie mixture into each of 12 (2-ounce) shot glasses. Divide pineapple evenly among glasses. Layer each glass with mousse and remaining cookie mixture. Garnish as desired.