Living in a great travel destination like Sonoma you should consider a duplex or triplex and operate the other unit(s) on AirBNB, VRBO, etc.

If long-term rentals don’t cash flow, short-term or mid-term rentals (Airbnb, traveling nurses, corporate stays) might work better.

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.

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. 

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.

There are many more and many more personal goals such as getting married and starting a family, adopting my first GSP dog, traveling to Wyoming and Montana and spending more time in nature, just to share a few.

And while short-term rentals are the big draw here, there’s also growing demand for mid-term rentals from snowbirds and traveling professionals, as well as long-term housing for the increasing number of permanent residents.Yes, higher interest rates are a factor, but the strong rental demand in the Panhandle often helps offset those costs.

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.  

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).