Vacation rentals in Hawaii

[Kyle J.]

I'm starting to look into buying a STR property in Hawaii and I know there's other members on here who have plenty of experience in this area that I'm hoping can chime in with their collective experience/recommendations/input on the matter.

I'm sure some people will think it's crazy to consider buying in Hawaii right now with everything going on with COVID, and that may be true.  However, I also have to assume this pandemic can't last forever and perhaps - because of the pandemic - there just might be quite a few current owners looking to sell at a discount.  So maybe there's some deals to be had.

Regardless, my wife and I have always planned to move to Hawaii full-time down the road, but we're now thinking about picking up a property a little sooner than expected and just living there part-time (a few weeks at a time) while renting it out as a STR the rest of the time to help cover the costs.

We do realize that until some of the current travel restrictions are lifted that any STR income may be limited (or non-existent) and consequently have set a tentative timeline for our purchase of 6-12 months out, which is why we're starting to do our research early (to make sure we're prepared to pull the trigger if/when the time comes).

Our favorite island is Maui, but we also like Kauai and would definitely consider that island too. (Those are the only two islands we're considering.) From my initial research, if we were to choose Maui, we'd be limited to a condo. (Not sure if Kauai allows STR of single family houses or not.) And on Kauai it seems we'd need to stick to one of the three designated VDA areas (Poipu, Princeville, or Kapa'a). Also looking for at least a 2 bdrm, 2 bath property since we'll also be staying there ourselves.

With all that being said, does anyone have any input/suggestions on the best areas to buy on these two islands?  And any other input/suggestions for the best types of properties or other things we should take into consideration?

Thanks in advance!