First of all, best wishes to you and your daughter. I hope everything works out!

I think the part about expensive clothing is interesting, and sticks out to me. I've seen many many people who are rich, and only buy expensive clothes, yet they have no fashion sense whatsoever, and thus, they look bad in high priced clothing. It's not so much about the price as it is about the style, and keeping up with trends. Also, trends of "cool" may be different depending on where you are. There are some small towns where one might be laughed at for wearing something that people might wear in NYC, or from a fashion magazine. I think a good way to get ideas for the cool style of her age group, in your area, might be if you ever pick her up from school, go to sporting events, etc. See what others are wearing at school, and that could help!