Very well thought out post, enjoyed reading it.
I will also have trouble buying smaller clothes, I have always been a very large girl, and within the last two months I have noticed changes with myself. Seat belts being looser, I can fit into the chairs outside of my doctors waiting room, machines at curves are so much easier for me to get in and out of, and the most important/biggest thing to me - the fact that I now have so much more leg room when it comes to sitting in the passanger seat of a car. These little changes, have made a world of difference in my thinking, just because I can now fit into things/more comfortably in stuff I was never able to before.
My friends have noticed I am shrinking, my family - my clothes, shirts in particular, are starting to become baggy on me. Pants are becomming loose. It's just amazing to me. I believe I will have issues shopping in a few months times when I start shopping for a new wardrobe, because I am so used to being in the biggest possible sizes. That is something that will never change for me, as I spent 12 out of my 22 years looking directly at the biggest end.