Or that loaning out money in a 15-20% environment to flippers, when the market has peaked (in your view) and refinancing has become much more expensive and harder to get, is a safer use of your principal?

It would behoove anyone interested in doing this to not only read up on the current regulations, but to also speak to people "on the ground" in Hawaii county that could guide them on the current environment- legally and politically.

If it were me, I would try and stay local just so I could self manage and increase my return in a higher interest rate environment.

By taking the time to review the lease agreement carefully, both parties can ensure a clear understanding of their respective responsibilities, ultimately fostering a positive and transparent landlord-tenant relationship.Landlord Responsibilities:In many cases, landlords are responsible for maintaining the overall landscaping and ensuring that the property meets certain standards, creating a welcoming and attractive environment for tenants and visitors alike.

In this moratorium environment look for people with recession resistant jobs and very low rent to income ratios.

I would use caution doing STR in an HOA environment unless it's a very STR-friendly HOA with bylaws that are difficult for the board to change. 

Rates have come down a bit and can work in certain situations - but this one looks like it potentially has the factors to make DSCR work in this environment (lower on the value range, multi-unit, creative leasing strategies i.e.

Interesting, though a 4.5M property would give me a bit of pause in today's environment, even in Hawaii.

Then look at all those factors and ask yourself how well would this investment fare in this type of environment/neighborhood.

Great cashflow market in a landlord friendly environment and large applicant pools.