When should I go on my Disneyland/Aulani adventure?

Kinda far out to make anything but a wild guess—I believe SWL is supposed to be open by summer 2019, so that could be an influence for you. Either for (if you are a giant SW fan and have to see it!) or against (if you are crowd averse—I suspect the crowds will be massive.)
Sounds like fun!
 
I would go as soon as I could. I really miss Disneyland. I've never been to Aulani. I remember when visiting that part of Oahu was peaceful and quiet. Ko'olina was our favorite beach location.
 



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