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.

Make friends and ask people to sit in on their deals.

Instead of having to enter personal info and upload an image of your driver's license for each Reporting Company, the Individual FinCEN ID allows you to input your personal data once and then link the Individual ID to your various Reporting Companies. 

We want to get a few rentals up and running and then (if all works well) begin bringing other friends/investors in to invest with us.

If you go that route, focus on stable, landlord-friendly areas with strong rental demand, and build a reliable team on the ground (property manager, agent, contractor).Regarding property management, it depends on your bandwidth and goals.

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

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

We are pet friendly and have some zeroscape backyards and have wording like "We are pet friendly with a fee, but please note although backyard is fenced there is no grass and certain areas contain crushed shell which could hurt your pets feet". 

Hi Joshua, I am an investor friendly agent.

They will get in touch with the property manager, let them know a complaint is filed, and typically give them an opportunity to make things right before opening an investigation.Have your friend look for a new PM immediately.Start by going to www.narpm.org to search their directory of managers.