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

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.  

It isn't impossible but as @Jimmy Lieu mentioned, there is a steep learning curve.Depending on your liquidity, out-of-state buy & hold rentals could be your best bet if NYC investing is out of the picture.

Statistically, I would bet that many of these properties could be at risk from a similar event before the reconstruction could even be completed.What is the new premium on a $5-10-20M insurance policy and how could it ever be recuperated during the life of the policy or length of the average 30 year loan? 

Don't get me wrong the market goes up more over time then down but if you happened to take out the loan when the market was at a high point this would actually be a win for you.  

The landlord must take to court a copy of the Notice of Eviction, the Affidavit of Service, the Complaint, the Summons, and any witnesses or evidence needed to win the case.

You bet.

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

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

I would bet the older homes will see a lot more appreciation than the newer homes, percentage wise.