I decided to make a third batch of TKO because I was not completely satisfied with the previous one. After experimenting with the dough a bit, I finally got the edge of the cookies to set better, and the cream filling better!
Never the less, this batch was 10X better than previous, look-wise especially! I do notice though the cream filling tastes better and gets a bit firmer after being in the fridge a bit. And after a couple days in the fridge, the cookies started to get lighter in color but they still tasted great! Yay!