My recommendation for anyone is to educate yourself, whether its Hawaii or elsewhere, because if you are aware of how STRs are regulated in Hawaii, this is far easier said that done.

Interest rates change, regulations change, in CA lots of fights happen, inflation happens, and just so many headwinds to fight thru as a developer. 

With land availability and zoning regulations conducive to new construction, developers are seizing the opportunity to build purpose-built rental communities in prime locations.

Not to mention, more HOA and possible gov't regulations on short-term rentals.With that in mind, as long as you pick an area that caters well to long- and mid-term (and possible short-term) rentals you'll have multiple exit strategies to employ.

But to be honest, with all the new regulations around documentation for cost segregation that has come out, I recommend having a professional do them.

It is the tenant's responsibility to ensure that the unit is installed, maintained, and operated in accordance with all manufacturer guidelines and local regulations.

You could drain and winterize but then it won't be available for guests.Many municipalities regulate hot tub maintenance for STRs.

The standard for raising rent varies depending on local laws, regulations, and rental agreements.

Don't forget, if you have owned a commercial property for a long time and have put a lot of money into it over the years, you may be able to expense many of those "improvements" with the Tangible Property Regulations (TPRs) of 2014.

When searching for landlord-friendly areas, it's crucial to consider local regulations, tenant laws, and the overall rental market's health.