I've been investing in one market for 10+ years and my vendor list continues to evolve and never had the mindset of assembling a team I can rely upon.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Will they continue paying market rent for a mismanaged property. 

I'm sure the BP community would love to be continually updated as well on your progress.

On their Wednesday's Zoom, they feature Show & Tell, so you can see the successes and questions of others.   

Interest rates atm seem quite high so will ride this out a bit longer (and ratios will continue to improve over time.) 

My goal is simply to make enough to show that my business makes money so I can continue enjoying living here.

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.  

I'd expect prices to continue to appreciate, so the longer you delay, the more expensive things may be. 

I also hope airbnb does not continue to get less host friendly.