Challenge: It's in a neighborhood (no HOA), and renting the entire property (sleeps 25 in total) caused problems in the neighborhood, due to noise and parties – so we only rent the separate cabins now.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

I have seen some properties on MLS that I contact my realtor and they may know right away the reason it isn't selling from showing it previously, or they can review the realtor comments that aren't viewable by the public on MLS.Other potential reasons I have seen properties listed on MLS for a long time. 1) Some investors may not be comfortable inheriting existing tenants.2) It may be it is a class C neighborhood. 3) Structural issues.

@Cheryl Abram, there could be a number of reasons why large investment firms focus on smaller investors.  

And still, neighborhoods can change, tenants can go rogue, things can break etc.I'm always looking for ways to help protect investors so I'm open to any ideas you have.

Market Range for neighborhood is $330-415k. 

Neighborhoods like Logan Square or Albany Park have seen growth in rental demand, making them potentially good starting points.

How do you know if a neighborhood is C class as an out of state investor? 

The picture they have on Zillow vs one of the several I have with the same view:Go to Redfin.com for your neighborhood.

It’s crazy how trying to stand firm can sometimes backfire in unexpected ways.