My agent is currently finding best rates with Travelers.   

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.  

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.

He currently travels often for work and resides in TN. 

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.

However, I am seeing more interest in MTR's and have a colleague that does well buying condos and renting out to traveling medical workers and foreign exchange students.  

I am primarily hosting traveling medical personnel because there is a lot of demand for these professionals in our area and because my units are suited to their needs.

Got back from traveling. 

We have about 22 full-time W2 employees in the office, approximately 40 traveling construction folks -- and managers and maintenance W2 employees at each community we own and operate.

They will raise more capital while on the guru traveling circus.