I am looking to do a oneWorld award with a large chunk of flights in December 2007, and the last leg on Janaury 6 2008. I know that the ~330 day window and 14-day hold create a bit of a sticky situation and my question is how best to time it considering availability.

Essentially if I put the ticket on hold now, then it will expire after 14 days, which is before I can get the final segments to open up for availability because of the 330 days. But, at the same time its around the holidays, and availability is scarce. BTW, I know that when I try to rehold at the 14 day mark, I will not be able to get availability on at least three of my flights so thats not an option.

Any other advice or should I just pray and hope that all my flights are still open come ~February 7/8.