Hawaiian real estate law differs from other western states significantly, mostly due to its monarchal heritage and the Bishop Trust influence.The basics are the same as would be in California; determine the condition of title ownership (individual(s), estate (including conservatorship, if appropriate) OR fiduciary acting for trust.Use a qualified private money equity lender to make a loan sufficient to buy out the cash-only beneficiaryThe legal community in HI and Big Island in particular is small.

I signed up for the paid version of Stessa through biggerpockets only to encounter flaws in their software, connection issues that have been ongoing for 10+ months, and basic feature missing that leave me dumbfounded. 

You also seem to have based your view of syndications on a sample size of 2 good outliers and based your disdain for direct ownership on a sample size of 2 bad outliers, and when someone brought that up, you basically said that you don't mind losing money as long as you spent no time losing it.The type of person that can lose 50k and be mad "for two days" and thinks that productivity has been lost if he spends a few little hours looking over a deal that could ultimately make more money than many people make in a year is a person that most cannot relate to.

In order to pitch for funding, we feel like we need to get a few basic ducks in a row.

Thanks again, @Tyler KeslingI love your enthusiasm, but you need to be careful about being so enthusiastic that you ignore the basics.  

Basically, it talks about the scope, timeline, and payment terms.

interest rates and prices are basically too high right now."

I ran some very basic numbers on option 1 and if you can get a ST/MT rental per your comments and other assumptions you list, this could be a deal for you.

Basically, the further you get away from the city the more potential for cashflow, but you're also dealing with a different tenant base that may be tougher to manage.

Umbrella insurance can be a smart way to shield yourself and your partners from potential risks that basic policies might not cover.From what I’ve heard, local insurance agents familiar with investment properties in your area are a great starting point.