My sister and I have both stayed at the Outrigger Waikiki at different times, and love it. I visited the Outrigger Reef when it was being renovated. I hear the latter (Reef) is much the nicer now with the updating. I really enjoy the restaurants at the Outrigger Waikiki, but the pool is smaller and crowded with few chairs though it does face the ocean. The rooms at the O. W. 18 months ago did not feel that "dated" to me ... they were fine, and immaculate but I understand the Reef rooms are lovely, large, super-new feeling, which is tempting. The rocky beach is not a problem at the Reef as I don't go into the ocean that much, and prefer Kuhio Beach area.
I'm thinking of staying at the Reef, and walking to the restaurants and beach area at the O. Waikiki. That's a very short walk as I remember??? What do you think, guys??? :-) The rates are about equal, last time I looked.