From my perspective, the money incurred is not the issue as it is manageable for most who are aspired to travel. It is the time involved and the physical demand on one's body (red-eyes, long back to back trips, etc etc) the part that I know I am not capable to push to the degree you have done.
Given the current economy, chances of having another DEQM look good. When that happens, it would the the time to jump in.
BTW, AA now charges for Challenges. I believe it is $200. It used to be free.