Preheat oven to 350 degrees F (175 degrees C). Grease 2 baking sheets. Beat butter, brown sugar, and white sugar together in a bowl with an electric mixer until fluffy. Beat in egg and vanilla extract. Combine flour, oatmeal, baking soda, cinnamon, and pumpkin pie spice in another bowl; stir into butter mixture alternating with canned pumpkin. Mix chocolate chips and pecans into the dough. Drop dough by tablespoonfuls onto the prepared baking sheets. Cut caramel apple circles into small, thumbprint-sized pieces and push 1 onto the top of each cookie. Bake in the preheated oven until lightly browned, 12 to 13 minutes.