I keep going back and forth between the Moana Surfrider and the Sheraton Waikiki.

We are a family of 5. 2 Adults and 3 kids (ages 8,5 and 2). I love upscale hotels. We will be celebrating our 15th anniversary and it is our kid's first time to Hawaii. We have been before, although prefer the other islands over Oahu. Due to flying over on AA miles, we are stopping in Honolulu first for 5 nights (then onto Maui for 10 nights - 5 in the Westin and 5 in the Hyatt).

Bottom line...which hotel should I stay at in Oahu on SPG points? We are gold level, so not sure if we would get an upgrade. The best room I could book at the Sheraton was the Ocean Front at 640 sq ft. Best room at the MS was a city view tower (half the square footage). Now I know most people are thinking that for a family, we should probably do the Sheraton.
I am just worried though because I think the MS looks much nicer and I like to feel like I am in a really nice place when travelling. We do not plan on spending most of our time in the room.

In the other 2 hotels on Maui, we will have slides and ocean veiw rooms. On Oahu, we will be moving around more. Going to Pearl Harbor, Hanauma Bay, touring the island (we will have a car), etc. I do like the pool better at the Sheraton, but as someone said...do you really spend that much time at the pool when the beach is right there (and we are going to be doing so much other stuff)....

Anyway, I know this is long winded, but PLEASE help. I am used to the finer things and we have stayed in a couple of Sheratons that have just looked really bad... I just want everyone to have a good experience.
Which is the overall nicest hotel of these 2 (the RH was a few too many pts)?
Which would be the best for my family?

Thanks for all the advice!