Keep in mind travel time, repairs, and lifestyle to manage the out of state rental.

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.

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. 

Please forward the contact information for any vendors with which you have experience or knowledge who can help exit a low-usage time share. 

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.

If there's a family member or friend in a similar situation, and you can both align on the initial plan (location, home type, price, usage/occupancy, etc) you can pretty easily get a co-ownership agreement in place and even a joint mortgage.The benefit here is it might open up your ability to buy a larger place in a nicer area which could lead to a faster rate of appreciation and overall better living environment. 

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.