My criteria is very strict.

Can regulations change?

All of this said, be sure to do your research on STR regulations first and find a STR friendly location.

Then a hiring increase for local regulation officials or private sector to assess housing quality & approve it.

I've consulted a few times over the years with planners and with the way I buy properties, my liquidity requirements, and my concerns about about how government overspending affects the future, makes me a poor candidate for IRAs and 401(k)s with the stifling regulations.   

I saw an example recently in Bloomberg about how local regulations can really shape a landlord’s experience, from what I’ve heard.

Build a strong team, prioritize cash flow, and take the time to understand the local market and regulations, especially for development projects.

To get started - I’d recommend connecting with local STR investors and researching Hawaii’s regulations.

BUT know your jurisdiction's regulation on screening.

To maximize returns, ensure compliance with local regulations, prioritize owning the land, and offer student-friendly amenities.