I travel for REI, businesses, my own business, and other interests related to work on average 2 days a month.I drop off my kids to school and then later pick them up with my wife after going to the gym every weekday during the school year together.

We also use Travelers and Proper.

Most are traveling professionals needing an alternative to a thousand dollar a week hotels.

Chris answer is spot on.I'll add "quick closing".You won't find investors easily, you have to go to a lot of meetups to build them.

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.  

He currently travels often for work and resides in TN. 

Fake income documents are easily purchased online, and inexperienced screeners often miss red flags.

My agent is currently finding best rates with Travelers.   

If they are professional, they can explain this quickly and easily.

Travelers, Farmers, Steadily are some who allow this model.