The CDT does go above timberline often, but not for long distances. It is a special experience to sleep above timberline when the weather is good. When I do that type of trip I use a Gatewood Cape from Six Moon Designs for above timberline and a ENO with SPE and Big Agnes Air Core for below timberline.
In my opinion, you do not need to go the ground full time to make your weight goals.
Check my gallery for a sunrise picture taken at 12,400 ft.