The current regulations per Hawaii DOH are that new cesspools and substantial repairs are prohibited.

It might be most valuable to establish those relationships before you decide to buy so that you'll be better prepared and that person can be there before and after the purchase. 

@Christian SmithHave you established clear investment criteria?

Rules, regulations, guidelines? 

Find an insurance advisor, establish a relationship, build trust and then thoughtfully follow their lead. 

there are alot of cities passing regulations on denying section 8 applicants as a form of discrimination. 

You are considered "disqualified person" to your 401k and assigning this contract to your 401k would be considered "prohibited transaction":https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-prohibited-transactions The proper steps would be:1) Establish and fund self-directed 401k2) Find and purchase investment

How would it work If I establish a new LLC to hold my rentals?

Also, check with your agent, I’ve been curious but haven’t investigated yet but seems like I heard the city has some landlord rules or regulations that may need to be considered.

@Liz Fisher, biggest thing to watch out for is the rules and regulations for STR but in a vacation area like that it shouldn't be an issue.