What are people's thoughts around tenant's Renter's Insurance in Chicago?

Are special assessments likely?

There are some VERY specialized strategies that can get around the problem, but they require buying out the former owner or one of the heirs. 

Every time I go to bid on property on civic source people are bidding it up to or over market value.

I am looking for some people to connect with in that area that may have more experience as we are out of state investors and have heard that Mississippi has great opportunities for cash flow and for people starting out in this industry. 

While this isn't common, I have know people that bought their first rental and when tenant moved out, had caused close to $20k in damages and skipped town after one year of living in place.  

You will be dealing with a bunch of people who want to see a return.

I guess, how do I decide where to commit my research to before contacting all these people and sticking it out.

I would network with contractors out in your area, or you can find people online (VAs).

In my area there is a nonprofit that provides free legal assistance for people of modest means in cases like this. 5.