Originally Posted by Boraxo
The 330 day strategy is not a "myth." Earlier this year, I called at midnight airline time (actually earlier in my time zone) exactly 331 days out and had no trouble securing 2 outbound seats in business class from US to Europe. It was not necessary to book a return flight at that time, since I received a 2-week courtesy hold. ^
After 14 days, I called back (again, exactly 331 days out) and booked my return flight. Got my first choice of flights, first choice of carriers (in this case a OneWorld member) and 100% satisfaction with no hassles.
I don't know how AwardPlanner operates, but it appears from this thread that they are unwilling or unable to perform as I described. If that is the case, why bother? By not following this protocol, you definitely risk losing your first choice of award seats, particularly on popular routes like Hawaii and Europe. Is it worth the risk?
AAdvantage, the program I am assuming you used for your award, seems to be more generous with award holds than most other programs. While AA typically allows a 2 week hold, most other airlines only give 3 days, if that. In addition, AA usually lets you hold a one-way while you wait for the return portion of your trip to come into the 331 day window. AA, in my experience, also has significantly better award availability than other FF programs and in most cases releases at least some award seats 331 days out (I had no problem securing two first class seats IAD - HNL 331 days in advance for my honeymoon two years ago and the return two weeks later.). Other FF programs release seats in a somewhat random fashion tossing an element of luck (unless you check everyday) into the equation, while others (such as CO) seem to have limited "saver" awards no matter when you book.
The OP's problem seems to be that he is using DL miles. I have little respect for the SkyMiles program. Next to CO's NonePass program, I have found that Skymiles are perhaps the most difficult to use for booking awards at "saver" levels. I started looking for a SkySaver award at 331 days out for a trip next October, coach IAD-ABQ. Can get there on desired day, but there are no SkySaver seats at anytime on the day I want to return. None. It's ridiculous when you are talking about a domestic coach seat that far in advance. I had my choice of flights on AA and UA, and went with AA.
As far as Award Planner, I am surprised to learn that they were not all over the 330 day advance request. It seems like a slam-dunk that they would want to dispense with immediately. This bit of news suggests that you are better off attempting to book on your own that far in advance and only pay Award Planner once you can not secure award seats within the first few days of the availability window. Incidentally, I have never seen any statistics about the % of requests that Award Planner successfully fills. Would be interesting to know before throwing money down a potential rat hole.