We also use Travelers and Proper.

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.

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. 

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. 

My agent is currently finding best rates with Travelers.   

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

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.

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. 

you can always call or email the tenant in regards to this matter. i personally smoke as well and just would want my tenants happy and not feeling accused as its a big problem with a lot of tenant v landlord situations around the country. you can always say you got a report of the odor of weed and was just verifying the smell with both tenants on the property. you can restate your conditions with smoking. you can always ask if they are legally able to do so as well (meaning medical card). depending on how you want to handle it, if you want to make it a legal warning to the tenant as well, you should write a written letter sent by mail stating you got a report of weed and this is a written warning in case this a problem down the road, you have evidence to show the court if it gets to that matter that this is not your first occurrence. best of luck!