One related general question I have is with regards to awards with a planned stopover (e.g. Hawaii - Continental US (stop) - Europe), especially if the planned stopover is a few months long.

Am I correct in understanding that one would need to wait until the entire itinerary was within the 330 day booking window? If so, are there any best practices to getting such an award at a lower level? In my experience, Hawaii would be long full by the time I was in the window for the full trip.

I'm currently in the early planning stages of such a trip on Star Alliance and am just trying to gather as much strategy as possible.

Thanks.