I would definitely book Aulani FIRST then book flights so as to not be stuck with expensive airfare. And since Aulani is a world away from WDW I wouldn't bother booking WDW at 11 months either. If I'm planning Hawaii I'm planning Hawaii. There would still be plenty of options left at 7 months for WDW if our plans changed. To me it would just be an unnecessary step and then ANOTHER unnecessary step to cancel that reservation.
I think early June at Aulani is harder than later in the month when the points go up
.of course availability could be harder if you're planning to overlap with July 4th too. I have booked studios at Aulani for August 2x now by being online promptly at 8:00 and ready to hit submit when the clock turned to 8:00. First time an OV then this time an IV because we had fewer points to work with this time. You should be prepared to be flexible with what category you book. The lower point values seem to go before OV. I booked this trip for
last August at 7 months and then at 8 days before we were to leave our DS had a medical emergency and wasn't allowed to fly so we had to cancel everything.

We ultimately ended up finding availability at WDW for 9 nights and drove down there instead so we wouldn't lose all of our points (they would've gone into holding and had to be used up by Nov. due to our UY).
We are also stopping at DL on the way to Hawaii and have managed to book a studio there 2x as well. I did "walk" that reservation both times tho since there are so few studios at VGC and getting that booked first was crucial to the entire plan. Everything hinged on getting that first. (I booked a week starting a few days ahead of when we really hoped to arrive then canceled off the first few nights later.) We leave in just under a month and now that we're so close I'm almost regretting adding DL because of the price of the park tix. The prices have gone up 2x I think since I bought tix for last summer. After being spoiled with our WDW AP price this seems RIDICULOUS. It will cost us just a few $$ shy of $800 for 3 days of park hoppers for 3 adults.

Last year I bought
4 days of hoppers for $825. They have really gotten expensive there. Stopping in LA for a few nights also added to the cost of our flights so be sure to look ahead at all of that before deciding what to do and be prepared to shell out a wad for flights. They have also gone up a lot since last year. The main reason we re-planned this trip was because most of our airfare that I booked last year was on Alaska Air and when we canceled last year they gave us credit for the flights good for 1 year!! Since we'd already spent over $2K for those flights it seemed silly to just waste it. But
everything else has gone up since. I had to completely rebook our flight from LAX to HNL becuz that was on a diff. airline and I paid 2x as much this year as what we paid last year. We're also going to Maui for a few nights and that inter-island flight went up as well. I would say if you can go next year
do it before it gets even MORE expensive.