Hi Mike-
While I'm sure the folks at AwardPlanner will offer a reasonable explanation about your situation, I thought it might be helpful to explain the '330 day' strategy.
Since a roundtrip itinerary must be confirmed before a mileage award ticket can be issued, you/AwardPlanner must actually wait until 330 days from the date of your INBOUND, not your outbound itinerary.
Further, while I am familiar with the urban myth of contacting the FFP call centers at the stroke of midnight on the 330th day (of your inbound travel!), the 8-10 hour delay in waiting for AwardPlanner to open at 800a MST should have negligible impact on the ability to find award space.
If you are insistent in securing space on your outbound travel on the 330th day, there is an alternate strategy. For example, using ORD-HNL Dec 5 outbound, HNL-ORD Dec 15 inbound.
1. Call on the 330th day (Jan 1) to book HNL-ORD as a 'phantom' outbound anytime before Dec 5. Book the ORD-HNL as your inbound on Dec 5.
2. Hope that the FFP will give you a a 14 day courtesy hold. If not, call them after the initial courtesy hold (say 7 days) and ask for an extension, which is typically granted.
3. Call on the 330th day (Jan 10) to book HNL-ORD on Dec 15. Replace the pre-Dec 5th HNL-ORD with the intended Dec 15 HNL-ORD.
Your ORD-HNL flight flipflops from an inbound to an outbound flight because you've replaced your HNL-ORD flight to being AFTER the date of the ORD-HNL.
Mike, I'm not sure you'll understand this methodology, but I'm sure the pros at AwardPlanner will.
This strategy allows you to actually secure BOTH your targeted outbound and inbound flights on exactly the 330th day!