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?