It's very possible/likely you won't make money with a deal like that, but it's better to break even or lose a few thousand on a deal (and learn a ton!)

I also assume people will leave the state entirely for fear of hurricanes and possibly move further north.

If I get a response on one of the properties, I will then assess the value and financial situation, see how much they owe and proceed accordingly with a short sale (if possible) or simply buy the house from them.  

My specific criteriaSFR 3BR 1.5+ Bath - purchase price less than $125kB or B+ propertyCash-flow positive (minimum 10% net cap rates with at least 1% rental ratio)$15k budget to rehab propertyRent out to family for long-term leasestrong appreciationlow vacancies / supplylow property taxeslow price to income ratiospositive demographics - low unemployment, low crime, high % renters, population growth, etc.Healthy local economylandlord friendly laws Those are possibilities for sure!

I am also in MA- You plans and goals are absolutely possible- and you are already saving very nicely.

We currently promote over 31,000 listing from all over US and $72B in inventory.The website has fantastic campaign in Google and is designed to capture as many buyers leads as possible but I am having problem monetizing it. 

If at all possible, I would get the flood insurance. 

Find a multi-family in an area turning around or going strong and it's worth 10 times the sfr.Sure you can possibly get good cashflow on a lower end multi in a bad area but you have to consider your exit.Don't let the fact that we're in a tight market force you into a property you will regret in the future.  

You probably want a 30yr fixed conventional. rates should be 4.25-4.75% or so for this type of loanand you will likely have to do 20% down for a conventional loanTalk to a lender and they will help you understand underwritingTalk to a realtor to help you the buying processTalk with other investors (as many as possible) in your area to understand market conditions

Is it possible to purchase the property through a conventional mortgage, personal loan, and my own money and then immediately refinance so I can pay back the personal loan?