Airbnb or pipe dream?

[Sumner Rabin]

My wife and I are desiring to buy a property on either Oahu or Kauai that will be an Airbnb. We currently have a good cash flowing rental in the same town we live in and would be able to drop around 100-140k as a down payment (or 25%) thru pulling cash out on said rental.  

Our preference is to Kauai as it’s just beautiful and more “exclusive” (homes in princeville specifically!)
I suspect Oahu to be a more difficult market to succeed in due to the sheer number of air bnb and hotels by comparison. Add in steep hoa and possible hoa restrictions. 

for those who have made investments in either location, what do I need to consider besides profitability that may be a deal breaker? Example- Florida has flood and hurricane issues which insurance premiums can run high. 

Is demand strong enough in Hawaii to sustain long distance air bnb operations?  

What if my business mindset was to not have an Abb, but an LTR instead? Oahu has a strong military presence- how much is rental vs ownership?

[Lake Lutes]

In late 2019, the government passed a number of different laws and restrictions concerning short term rentals (defined as less than 30 day stays). Check out this website for more details: http://www.honolulu.gov/dppstr...

In summary, there are very specific areas/buildings allowing short term rentals, and the taxes and fees for those units are much higher than non-short term permitted properties. A few properties got grandfathered in around the island but it is next to impossible to get a new property approved for short term renting.

Long term rentals (30+ day stays) are great options and the right properties/areas have extremely high rental demand.