I recently obtained my HI real estate license to access the MLS and assist with my personal house-hunting needs.Does anyone know of a more boutique brokerage on Maui where I can hang my license with minimal overhead and without the requirement of going through a mentorship program?

Very few people have reached financial independence...and others that have reached it that keep working do it for personal satisfaction.Incidentally, most of us consider real estate, done properly, to be lower risk than the stock market, which is why we invest in it.

Attorney for HOA said it was pretty easy to find the HOA address and the county should have done more to hunt them down. 

Make sure to include proper disclaimers. 

So, proper screening is EXTREMELY important!

The specialist I recommend you have is an attorney to properly draft the documents and a title company to facilitate the deal.

Maybe you could have a timber guy strategically come in and cut some of the timber down so you could get some cash and then sell to someone looking for some hunting land.  

Quote from @NA L Harrison: It is irresponsible of you to take in animals you can't properly house.

When you analyze a market properly (1% Rules aren't properly), you're analyzing all the properties in that market at the same time.It's even more dangerous for newbies to use any Rule of thumb.Rules of thumb are nothing but shortcuts, which seems to be the growing method of doing anything now. 

STR's, if done right, are viable long term investments meant to cash flow at a reasonable enough level to properly maintain and improve them.