Aloha and welcome to BP @Garrett Hilt--
There have been some very valuable comments posted on this thread...some a bit more self-serving.
You mentioned [Due to my work and family situation, I am really interested in the vacation rental business].
Can you elaborate a bit? Are you in the resort biz already (with direct vacation rental experience), do you plan to live in it at some point in the near to mid term, or do you just like the concept of renting out a place that allows you go play when you want?
The one comment about Hawaiian vacation rentals stated that they "have achieved an 80% occupancy rate average over the last several years".
My response to that is that "all boats rise on a high tide".
Being that resort destinations generally rely on discretionary $$ to generate demand/revenue, that demand can vanish very quickly. I have been going to Hi for more than 50 years, lived there for a period, and have seen major price fluctuations (up AND down) as a result of the impact of demand drivers. Some of these drivers, like general US economic recessions, can reduce domestic discretionary $$, leading to corrections in the market.
But there are other demand drivers which can also impact values...such as the GDP of other countries, strength or weakness of the dollar, etc. (especially as it relates to Japan and Canada)
Being from California, I have seen first hand, when we catch 'cold', Hawaii catches 'pneumonia'!
So, tread lightly, my friend...while it is sexy to say you own a condo on Maui, it may not be in your best interest to do so.
Aloha hui hou