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.

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.

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

Cost segregation and advancing depreciation has its pros and cons depending on what the individual investor's goal is.

I believe sometimes a bad experience is more reflective of the individual than the company. 

There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

It will cut down on the fake accounts created to promote certain individuals, markets etc.

Use caution when borrowing against your stock portfolio, especially if it's a high volatility portfolio comprised of individual companies.

It was suggested that we create an operational company that will lease rooms to individuals in recovery.

Could be.I think that for most individual American investors leverage is a critical tool.