Preheat oven to 350F (175C) and prepare 2 8″ cake pans by lightly greasing and flouring the sides and lining the bottom with parchment paper. Set aside.
Combine butter and sugars in the bowl of a stand mixer (or in a large bowl and use an electric mixer). Beat until well-combined and light and fluffy.
Add oil and beat to combine.
Stir in pumpkin.
Add eggs one at a time, stirring well after each addition.
Stir in milk and vanilla extract. Scrape down the sides and bottom of the bowl to ensure ingredients are evenly combined.
In a separate, medium-sized bowl, whisk together dry ingredients (flour, baking powder, baking soda, salt, pumpkin spice, and cinnamon).
Gradually add dry ingredients to wet, stirring until completely combined (be sure to scrape down the sides and bottom of the bowl). I prefer to do this with a spatula to avoid over-mixing the batter.
Divide batter evenly into prepared cake pans and bake on 350F (175C) for 40-45 minutes, or until centers spring back to the touch and a toothpick inserted in the center comes out with few moist crumbs or clean.
Allow cakes to cool for 10 minutes and then invert onto cooling rack and allow to cool completely before frosting.
Cream Cheese Frosting**In a large bowl, combine butter, cream cheese, vanilla extract and salt and beat until smooth, creamy, and well-combined.
Gradually add powdered sugar to mixture until well-combined, smooth, and light.
Once cakes have cooled, ice/assemble cakes by first leveling the cakes (I linked th the leveler I used in the "equipment" section above), generously icing between layers, applying an even layer on the top of the cake, and then applying a scant, semi-naked layer around the outside of the cake.