I know I have very few posts on here but, in this case and considering I've was on an annual vacation for more than a decade to the Islands I would suggest... The Islands, for obvious reasons have a select inventory that is only of concern during peak travel times.

If your trip is 'upcoming' then I would think your consideration is valid if you're in/out during high occupancy times (?-mid February). Otherwise, and especially on Kauai, the inventory isn't likely to differ much based on the expected travel vacation travel patterns.

In short, if you're upcoming trip is any other time than mid-February then I don't expect you'll be gaining much advantage by your suggested ...gaming the exec.aisle path.
HNL or OGG might be a different story but not really in Kauai IMO.

Regards,
.cj