I've also heard of requirements to own for at least one year before you can use the home as a STR.Hawaii is a leftist state that doesn't protect private property rights.

Actually the IRS does not tell us what we can invest in, only what is disallowed (life insurance contracts and collectibles).Allowable investments for SDIRA investing include the following:Residential real estate, including: apartments, single family homes, and duplexesCommercial real estate Undeveloped or raw landREITs (Real Estate Investment Trusts)Real estate notes (mortgages and deeds of trusts)Promissory notes Private limited partnerships, limited liability companies, and C corporationsTax lien certificatesOil and gas investmentsPrivate stock offerings, private placementsJudgments/structured settlementsGold bullion Factoring investments

I am also a lender, with Chase Bank, but want to expand my knowledge on hard money and private financing options.

We use private investors and offer them 20% APR, with 10% return guaranteed, paid as a balloon. 

@Luke H.Hi Luke,  As a private money lender myself I will focus on one element of your deal---5 years is a long time to be finally paid. 

@Brian Rocha  Hi Brian---I just sent to you a private message.

Now most of my deals are a combination of our business money, bank money, hard money, and private money.  

And if your investor friend’s private loan helps fill in any gaps, it might be worth considering that short-term pain for long-term stability.What do you think you’d focus on first... paying off that line of credit as fast as possible or jumpstarting the renovation to boost cash flow right away? 

For example searching on keywords in both the description and private remarks that aren't shown to the public. 

Eli,If I were you I would look into Subject Two, Land Contracts on Properties that are free and clear and Raising Private Money!