Many property owners rented, and decided not to rebuild, but to sell their homes and use the money to invest, travel, etc., staying in rentals.

Seasonal Slowdown (With a Twist)The holidays always lead to a slower rental market as potential tenants prioritize family, travel, and gift-giving over finding a new home.

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.  

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. 

He currently travels often for work and resides in TN. 

My agent is currently finding best rates with Travelers.   

If you're prospecting the entire coast, just keep in mind travel times for tours and be mindful of the weather.

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.

That said, we have traveled a lot and stayed in wonderful Airbnbs over the years and have always dreamed of creating an incredible experience for someone visiting Minnesota with a short-term rental as well, so we are definitely open to that idea and have some great experience as to what we know would provide an exceptional short-term rental experience. 

If you need income that'll be a certain set of options if you're trying to free up time and not be responsible for property management because you're planning to travel in retirement that'll be a different direction.