Where do you live and how far would you want to travel to manage the property? 

We also use Travelers and Proper.

This was pretty confusing regarding "Core" Stessa features, BP should probably refer to it as "Essentials" package (free tier).

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.

To simplify the existing lease I thought about asking the tenant if they would be ok modifying the addendums to get rid of the resident benefit package and the building protection plan. 

I guess so they could tell Chris (who seemed to be travelling all the time) they were still working.I met with the original contractor, the one that had told me to come to Spokane, and he explained that he had slowed down the work because he wasn’t getting paid on time.

Do you want to have airbnbs all over the country and travel between each of them and living an adventurous life?

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.  

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.