But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Seems odd as this would be a business expense for my business.  

That’s the best bet.

Airbnb gives you the best bet at getting both. 

agree .. other wise its just the bottom feeders looking to take his equity from him  with couching it as a rescue.. his best bet it to sell if its owner occ the profit is tax free .. regroup and start over.. 

This level of infrastructure typically exists only in cities with metro populations over 1M.SummaryThe odds of living in a city that meets all the requirements for financial freedom are low.

Do you need or want monthly cashflow, tax write-offs, betting on appreciation,....   

But, I bet-ya it's also effective.  

Moving forward scaling with hard money loans may be the best bet and would avoid the headaches of living in a construction project. 

You bet.