Quote from @Chris Hertig: We recently purchased a multi-family property and have someone living illegally in an uninhabitable, detached garage. 

My lease requires renter's insurance which should cover loss of use if the unit becomes damaged/uninhabitable, but I don't think renters insurance covers costs of living expenses incurred during just an evacuation.

This is a very rough comparison, for Maui island only, but in 2012 median condo price was $356,158.

Quote from @Makani Donaldson: From what I understand, different islands or cities have different rules, and they are getting stricter.

Island. nothing installed in your island. 

I got about 1.2M sitting and would really like to put it to work, I only own 1 SFR in Staten Island.

Is this strategy something I could deploy in a high entry area like New York/Long Island? 

I'm from Long Island, NY starting my journey in Real Estate.   

I would love to maximize cash flow but also do not want to be left on an island if there is damage. 

A BRRRR is when you buy a house (often uninhabitable) and rehab it BEFORE you rent it out. 2.