That said, we have traveled a lot and stayed in wonderful Airbnbs over the years and have always dreamed of creating an incredible experience for someone visiting Minnesota with a short-term rental as well, so we are definitely open to that idea and have some great experience as to what we know would provide an exceptional short-term rental experience. 

If you're prospecting the entire coast, just keep in mind travel times for tours and be mindful of the weather.

I am in the Tampa bay area now but grew up in Kentucky and travelled to Indy many times!! 

Meaning you can spend the time traveling to the market(As we did for 18 Months once per quarter) or you can seek a reputable operator in the market you want to invest in and leverage their team. 

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. 

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.

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.  

My agent is currently finding best rates with Travelers.   

He currently travels often for work and resides in TN.