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.

I think younger travelers and groups with younger guests find this more appealing.

A place that is easy (and hopefully) inexpensive for you to travel to a couple times per year to check in on things.  

We certainly haven't ruled out investing in Wisconsin, but we have friends and family that live in both CLE and CBUS, so we travel to those markets fairly often.

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.  

We also use Travelers and Proper.

He currently travels often for work and resides in TN. 

My agent is currently finding best rates with Travelers.   

Right now focused on Charlotte & Raleigh, NC, but also considering some of the advice above of sticking with markets I have friends/family in and travel to frequently. 

i don't know how you BRRRR out of state unless you're planning on traveling there frequently to oversee it.