If you're a steak person, the casual restaurant by the pool (Naupaka Beach Bar) cooks up a decent New York Strip. Compared to the cost of other food options here, I think it was reasonably priced for the quality. iirc, $50 including an extra side of fries, a fancy soda and extra tip. I've had worse strip steaks in NYC steakhouses.

About the late checkout/ early check in: I was able to check in around noon, and you can stick around at the property even after checkout. They provide lockers and showers for those wanting to hang out after check out.