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.

In my experience, and based on what I've read here, there's nothing else you can do.

The following definitely falls under the YMMV category, but it's worked for me twice...

As my complex (15 or 16 segment) held itinerary is about to expire, I call an AAgent and explain that I would like to cancel the itinerary and have the AAgent immediately rebook all segments in order to gain another two weeks to finalize my trip. (Yes, I understand that all my released flights may not go back into available inventory, but that's a risk I'm willing to take because the itinerary is about to expire anyway.)

Faced with rebooking such a complex itinerary, the AAgent cheerfully offered to extend the original booking by another two weeks.

Great advice LRD, I'll try that one