Spending on expensive upgrades is not the answer to improve your tenant base in this type of area.Keep the homes habitable, clean, and safe. 

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

I think younger travelers and groups with younger guests find this more appealing.

We also use Travelers and Proper.

i don't know how you BRRRR out of state unless you're planning on traveling there frequently to oversee it. 

He currently travels often for work and resides in TN. 

My agent is currently finding best rates with Travelers.   

My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family. 

Combining short term rentals and a venue is a huge advantage because guests would not have to travel far and you could offer better rates as part of a event package.My current venue focuses more on baby showers, content creation and birthday celebrations rentals.

Monitor your spending habits to make sure you’re consistently putting money aside for both the short-term and long-term costs of real estate.