I once was in the pool at the Coral Building for Lawai Beach Resort on Kauai (Koloa, Hi near Poipu Point), years ago. As I talked with others in that pool as we shared timesharing experiences, I realized I was the only person in the pool that did not own more than 1 week at this timeshare. One couple, both teachers, owned 4 weeks and were using them yearly in a row and sometimes let family use some of them. Also, one couple had a car parked in the Coral parking garage for their own use when they came for multiple weeks. Sure make a lot of sense to stay multiple weeks since flying to Hawaii is not cheap.
My spouse and I own 1 week on Maui and 1 week every other year on Kauai. We found it was cheaper round trip to fly to Lihue, Hi (Kauai) and then fly back, after using both weeks,back from Kahului, Hi (Maui) with Alaska airlines. The savings is enough that we then used Island air to hop from Kauai to Maui. Island Air went out of business since we were there last and this month we got a direct flight with Hawaiian Airlines for $103 each for next April.
I now own at the Banyon building (Lawai Beach Resort). So I recommend owning two plus weeks in a row either way. Two weeks plus at the same resort or island hop for two weeks in a row at different islands.
Of course, before I was retired two weeks in a row was hard to obtain. Now retired it makes perfect sense.
Many of the midwestern owners come to Hawaii to skip harsh winters. But some of the Hawaiian islands, Dec and January is the rainy season. Lawai Beach is on the southern coast and not as much rain.
I did a lot of research and I try to go the last two weeks in April. Demand is down and one can pick which room one wants to have at Lawai Beach. Flights are cheaper after the flurry of spring break. Weather is nicer.
I realize this does not work for everyone but applying some of this logic to your own situation at resorts you like I recommend more than 1 week. When I pick which room I want, I walk into reservations while I am there
and book it 2 years in advance for the next time we are coming back.
Lawai Beach Resort originally was a Shell Property (now owned by Wyndham) but now has a very good owners organization and great staff that run it.
Resale prices are very reasonable. These are not fixed weeks at the Alii or Banyon property. So things are quite flexible.