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.. 

Best bet would be a “partnership” with a monied individual looking for a high risk/high return passive investment with you providing the “active” part.  

I'm betting he'd drive to that area.

That’s the best bet.

You're best bet is to call a few brokers local to the area and see what they can come up with.It's definitely going to be a surplus or excess carrier that will do it and the premiums will be high. 

Airbnb gives you the best bet at getting both. 

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.  

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

I like this, bet on the jockey more than the horse kind of situation.

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