Turns out after some more investigating my theory was correct.  

Oh - and be sure to set up some keyword alerts - especially for "Chicago" so you'll be notified when people mention it here in the forums.Thanks again for introducing yourself!

However, i searched Craigslist to investigate what monthly rents people were asking for and was surprised to find 1000's upon 1000's of SFR's for rent.These are my assumptions about the area. 

When I explore a new area for vacation rentals, I use three strategies: Airdna reports- these give a good overview and are a quick way to know if it's worth more investigations.

There are a host of products out there that would work for your situation and you should investigate a few of them because one may fit your goals better than another.  

The keyword is "undetectable," so not testing out the system to identify an obvious issue would result in a denied claim. 

Here are some recommendations for you:Find and connect with other BP members that are in your area:http://www.biggerpockets.com/meetSet up keyword alerts to be notified of the topics that interest you:http://www.biggerpockets.com/alertsRead Beginner’s Guide:http://www.biggerpockets.com/real-estate-investingWishing you the best!

Not sure what the REI friendly banks are around southeast MA...Keywords: Boston, Quincy, Bridgewater, Brockton, Plymouth, Providence, Fall River, New Bedford, cape cod, 

Here are some good places to start: http://www.biggerpockets.com/meet- find and connect with other BP members that are in your area.http://www.biggerpockets.com/alerts - Set up keyword alerts to be notified of the topics that interest you.And, of course thehttp://www.biggerpockets.com/forums - ask any question about real estate!

@Justin Harford contact the investigating authority local P.D. or Sheriffs department.