I think that area is going to do well with the new complex’s going in at 5th and Main. 

Yes, people are still using Airbnb but if you are basing your main long term investment around it I would really consider other exit strategies and alternative monetization

I deal with mainly higher end units which get phenominal cash flow, but the problem is there isn't a lot of good comparable data.

@Alina Trigub I mainly work with web applications.

Obviously there is a lot of factors left out of this (will bank approve, you name another etc) but just from a theoretical standpoint is what I proposed (using tenants $300K down payment as a down payment for my traditional loan) illegal or just not feasible and I've completely missed something here that more experienced people can explain to me when they are done having their chuckle.  

I’m looking to meet other investors in Hawaii, mainly on the Big Island, and my goal is to get my first deal under contract within the next year. 

I started a contracting business doing general contracting with a focus on roofing with a business partner i met at my main job.

Work into your numbers what you think it will need in deferred maintenance right away, and what it will need each year from then on.Those are the main things I think of, but judging by the rent to price ratio, it looks to be a great start (at least in Nashville it would be)!

My main goal will always be to build a portfolio of long-term buy and hold investments and to acquire properties with as minimal cash invested as possible.

I have heard that though most things are taken care of as you stated the biggest uncontrollable factor is the HOA.