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

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. 

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

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.  

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.

They have a revolving door of people. 2 months down the road and no one know you and what they promised.

A lot of people put off getting into real estate because they don't have the money.