@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. 

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

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.

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

Meanwhile, we were paying a crazy high interest rate to our private investor who had funded the purchase of all the homes.

A recent article on Islands.com highlights Henderson's charm, from its historic petroglyphs and post-WWII transformation to its thriving arts scene, boutique shops, and outdoor adventures.

When people bring up Subject To (very risky) and private money it's usually because they have seen a lot of scaling content.

There are other ways around this such as seller financing or private money lending but that is an obstacle you should be aware of. 

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

My goal is to acquire and stabilize these larger properties using private lending to fund down payments and renovations while executing a BRRR strategy.I’d love to connect with private lenders or experienced investors who’ve used private capital for similar deals.