Hi! We live on the East Coast (near Baltimore), and go to Oahu every 2 years (we own 2 weeks at Marriott’s Ko Olina in 2 bedroom units, so 3 years ago I did the lock off and had the first 2 weeks in the studio then another 2 in the one bedroom portion). We also lived on Oahu for a few years in the 90’s. With such a long travel time, 2 weeks at least is best for us.
What major airports do you live fairly near? There are some nonstop options, like Chicago. I grew up in St. Louis, and there was back in the day a nonstop there, but that’s long gone. Took it a few times. We have always gone from BWI to either Atlanta, Chicago, Dallas, or MSP. Next trip we’re going to drive out to Dulles (well, take a shuttle) and do United’s nonstop, as we’ll arrive earlier, they have Polaris lie flat seats, and it will be less travel time. Most trips, by the time we get up, get the super early flight from BWI, land, get rental car, stop at Target for some supplies, and get settled in, I’m up for nearly 24 hours and it is exhausting! Still worth it!
Waikiki will have a TON of options, and it’s a great idea to start a trip there. You won’t need a car there, traffic is awful, parking fees are high, and all of Waikiki is walkable so it won’t matter where you are, you can walk everywhere. We’ve stayed at the Moana many times, and can walk to the Hilton Hawaiian Village and back easily. We’ve also stayed at lots of other hotels (Kamaainas get great rates so we did lots of staycations for the weekends). That part will really depend on your budget and what amenities you want.
Any airline specific questions, I’d be glad to help with, as we’ve been back and forth many times. We’ve done coach (ugh), comfort plus, and first. Now that I’m in my 50’s I’m not doing coach any more, and like lie flat seats (especially since the return is always a red eye and I need at least a couple hours of sleep). We’ve done American and Delta, they’ve both been fine (once ended up on Hawaiian but it was an old seat and awful experience, but that was a unique trip as we came into Hawaii from Seoul and long story).
I’m sure you will love Aulani, as we love Ko Olina. It’s basically now like our ”vacation home”, and we don’t tour around much, just enjoy the resort, hit up the Swap Meet at the stadium, drive back to Kailua once to eat at local spots we loved in the past. Unless we’re staying in Waikiki ahead of time, I avoid it now. The traffic is too much for me, lol.