The down side is that STRs are more work, need to furnish it, pay for utilities and WiFI but in the right market (vacationers and business travelers) it could work. - If I were looking at cash flow as a really important important metric, I'd consider starting a business.

Walking score of 95.Pre COVID rental numbers:Monthly gross rent $15,250Cap rate 7.1%Future rental numbers:Estimated Monthly gross rent after current tenants move out $13,950Cap rate 6.5%Because monthly rent looks to be about 20-30% more if you rent by the month, I am considering renting out my duplex for monthly rentals on Airbnb/other sites and potentially for travel nurses (ideal because several hospitals are walking distance to my house).

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

I'm looking for someone is willing to spend time with me and maybe teach/talk/travel around the city some.

We also use Travelers and Proper.

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. 

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.  

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.

My agent is currently finding best rates with Travelers.   

He currently travels often for work and resides in TN.