I am guessing that both of you are talking about award stays at the JW Marriott Ihilani even though that was not explicitly stated. While upgrades are possible, they will probably go to paying Platinum and Gold Elite guests first (YMMV). Also, there is no such thing as an auto uprgade as all upgrades are based on availabbility. If the hotel is sold out then nobody will get upgraded.

Now with that said. If an Ocean View is a must, then book an Ocean View otherwise your expectations may be dashed which could result in an unpleasant start to your trip. I have stayed at this property a half dozen times, all on paid stays, and I have always booked a mountain view room. I have always gotten upgraded, but I would have been content had I not.

Watever you do, have a wonderful time.