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.

You should have updated the address in the lender portal to your physical address so you receive statements and late pay warnings.Only way this scenario happens is if you do none of these. 

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.  

You might have to dig into off-market deals, though, since inventory is tight.Multi-Family: Always a safe bet if you can snag a good deal.

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.  

If im out of state, does it make sense to join social media groups, etc. to accomplish the same thing without being physically there? 

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

You aren't the insured in this case.Renters insurance does not cover the physical damage of the real property - it covers the tenants personal property and other things. 

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. 

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