I have quite a few clients who self manage their vacation rentals from the mainland.Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):  If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation.

I require a social security number to run a credit/criminal background on every adult.

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Easier to rent:  Two bedrooms attracts fewer occupants (not tenants) vs a 3 bedroom where often that extra bedroom is housing an adult kid, dead beat family or friend.  

@Jagan ReddyI'm not a CPA or a cost segregation specialist, but I do know that if you are not designated as a  real estate professional, then you can only offset passive income by your passive losses.Qualifying as a real estate professional is more challenging than most people want you to think.

And since you are out of state you will need to be open to suggestion on design, size, etc.

Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

I lacked the architectural knowledge to design my own.

@Dylan S. seek advise of a CPA, but form an LLC and get a S-corp designation. 

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