Adjust an oven rack to the middle position and heat the oven to 350°F. Grease or line a jelly roll pan with parchment paper. Whisk the flour, baking powder, baking soda, and salt together in a medium bowl. Set aside.
Place 1 1/2 cups of sugar and the cream cheese in a large bowl. Pour the warm butter over the sugar and cream cheese and whisk to combine (some small lumps of cream cheese will remain but will smooth out later). Whisk in the oil until incorporated. Add the egg, milk, and vanilla; continue to whisk until smooth. Add the flour mixture and mix with a rubber spatula until a soft homogenous dough forms. (I usually use my KitchenAid mixer for all of this). Alternatively, you can buy a roll of refrigerated Sugar Cookie dough and use that for the crust.
Scoop the dough onto the jellyroll pan in mounds, then use your hands to press it evenly across the bottom of the pan. Bake until the edges begin to brown, about 14-18 minutes, rotating the pan after about 8 minutes of baking. Let cool for at least 20 minutes.
Make the whipped cream: Combine the cream and 2 tsp sugar and whisk, using a handheld mixer, whisk attachment on a stand mixer or a normal whisk (the option of choice if you're looking for a workout before you eat dessert). Whip the cream until soft peaks form. Remove and place in a separate bowl. (Alternatively, you can use 2/3 cup cool whip, thawed, and skip this step).
Combine the softened cream cheese, 1/2 cup sugar, and vanilla; beat until smooth. Add in the whipped cream and mix until combined and fluffy. Spread evenly over the cooled cookie crust.
Sprinkle assorted fruit over the cream - as much as you desire. For a fancy touch, grate part of a chocolate bar lightly over the top to create chocolate shavings.
Source: recipe from my second mom growing up, Mrs. West. Cookie crust from America's Test Kitchen