Our family loves Hawaii. We have relatives who love it so much that they lived there for a few years, and others who used to go visit regularly ever single year, sometimes two or more times a year. We used to go regularly until our son was born, but the thought of making that trip with a younger than 5 year old child fills us with horror. We have friends who risked it, and although the child enjoyed the trip, they really didn't...
Our family has debated buying either a condo or a timeshare there for years and years. Our son's birth postponed the debate, but has not ended it. We're waiting to adopt another child right now, and that will postpone the debate again for a bit... However, it is almost inevitably going to happen at some point., the question is not if we'll get something, it's what we'll get.
We're waiting to see
point charts, annual dues, and buy in costs before we commit to DVC Ko'Olina, but right now I'd say we're likely to own there. Our tentative plan is to buy enough points to get a 2 bedroom ocean view every three years. As I've posted before, we like the idea of getting it through DVC (so we're definitely holding off on buying anything else in Hawaii for the time being) because if some years we don't want to make the long flight, then we can use our points at WDW.
We don't mind using Oahu as a main base, as we can get a direct flight from Houston. That makes the trip far less painful... We're likely to spend most of a week on Oahu, then do a few days on another island. DVC should work well for that, particularly since they aren't likely to require exactly a week.