Owning a vacation property in Hawaii has been a lifelong dream of mine, and it seems that this dream may also be able to generate some tax savings for me.I'm looking for a 2 bedroom or more condo in a resort-zoned area of Hawaii, specifically the Waikoloa Beach or Mauna Lani Resort areas which are already resort-zoned.

Moving in and out of the current home could cause red flags for the lender.

We have ask for a mutual release and return of our $2,000 earnest money due to the fact we no longer feel it is a safe area because of the break in and there have been a few other red flags along the way.   

The first step is to get out of your comfort zone.

That will raise the eyebrows of tax people and zoning and they will come knocking.Neighbors will often be savvy when it comes to STR's and they will call the city.

Also, remember an RAL will likely be located in a residentially zoned area, not a commercial zoned area like a big box ALF would be.

Problem here is, apart from the zoning restrictions of STR, purchasing a property is extremely expensive.

Get out of your comfort zone.

Wouldn’t I run into issues with zoning if I were to do this?

It looks like the ADU has not been properly zoned to be considered it's own unit, so according to the tax assessors report the property is a 3-bed SFH.