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.  

Multifamily real estate has traditionally been a stable asset class, and the Washington D.C. metro has traditionally been a stable market area, making the two together a good safe bet, especially for anyone with a long-term view of their investing strategy.

.- If you hold a rental until death, you can pass it on with a stepped-up cost basis, limiting captial gains if then sold (limited by inheritance tax limitations).Too many newbies on this site trying to replace their day job income via "passive" real estate investing w/o digging deep enough to understand how it really works.

Honestly, upgrading to a commercial-grade stackable setup like Speed Queen or Maytag might be your best bet.

But using lockbox at each site could help.

@Sue Duvall I suggest you go to a site for the residential assisted living academy in Phoenix.

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

I attempted to provide the most transparent and up to date information on this site. 

They list properties on their own site, plus Airbnb, VRBO, Booking.com.

If you could furnish the rooms, I'd say that is best bet for cash flow.