A mid-term rental could be an great option during the 6-7 months you're away since it appeals to traveling professionals, remote workers, or individuals relocating and offers stable income without the constant turnover of short-term rentals.

Ideally I'd like the ability to invest in individual stocks of my own choosing (fractional shares is a plus), a diverse option of index funds, and ETFs.Has anyone found a great banking option to have the most flexibility with your HSA investments?

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 can find numerous other similar homes for investors.

My core investing philosophy is pretty simple, and has done very well across almost two decades and numerous cities:1) Invest in cities with population (and job) growth2) Invest in parts of the city where household income is near the median (or slightly below)3) Invest in properties that provide cash flow from day 1 Thank you for sharing that. 

They have people invested in individual properties, especially students. 

I would echo this, it is a great REIA and the best place to find local, like-minded individuals and resources. 

This is a fine needle to thread because at this size, you very quickly start competing with high net worth individuals who are seeking summer homes. 

Quote from @John Morgan: I’d do individual cash out refis on them to scale up.

I’ve got numerous other examples.