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.

Shop LTV (or cLTV which is combined Loan To Value, basically your first mortgage and 2nd mortgage combined loan to value), rates, payment terms, time to close,  and draw period (how long you can go into and out of your heloc). 

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

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.

The "sweep" strategy is part of basic financial education in some countries other than the U.S.

I have actually been thinkin about cutting losses honestly, I am not sure this is the best investment I could have made as my first but worried about how much of a loss I would have to take.It is meant for S8 for sure, I would have a stringent application process, and give the neighborhood a C from my research.I invested there because it was the first deal that basically fell on my lap where the mentor works with agents that Seller Finance deals, it was only $3k down and had thought the proximity to St.Louis would be attractive to tenants also.I effed up on waiting to post for rent until after all repairs and the COO for sure.  

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.

Also illegal for the entire school year, if the tenant has kids in school. 

My goal is to gain a solid understanding of the process, master deal analysis, and ultimately close my first deal.Right now, I’m focused on learning the basics — from finding motivated sellers to building a strong network of cash buyers.