Heat oven to 375°F. Place pie crust in ungreased 9-inch glass pie plate as directed on box for One-Crust Filled Pie.
In 10-inch skillet, mix 1/4 cup brown sugar and 2 tablespoons butter; cook over medium heat, stirring occasionally, until sugar is dissolved. Add apples; cook uncovered 12 to 15 minutes or until apples are tender. Drain; set aside.
In medium microwavable bowl, microwave caramels and half-and-half uncovered on High about 2 minutes, stirring after 1 minute, until mixture is smooth.
In large bowl, beat cream cheese and 1/2 cup brown sugar with electric mixer on medium speed until smooth. Beat in egg, 1 1/2 teaspoons vanilla and 1/4 teaspoon pumpkin pie spice until smooth. Stir half (about 1/2 cup) of the caramel mixture into the apples; pour into pie. Mix pecans and chocolate chips; reserve 2 tablespoons for topping. Sprinkle remaining pecan mixture over apples. Fold remaining caramel mixture into cream cheese mixture, and spread over pecan mixture.
Bake 40 to 45 minutes or until filling is set. Cool on cooling rack 1 hour. Refrigerate 1 hour. Meanwhile, in large chilled bowl, beat topping ingredients with electric mixer on medium speed until soft peaks form; spread over refrigerated pie. Sprinkle with reserved pecans and chocolate chips. Refrigerate until ready to serve. Cover and refrigerate any remaining pie.