It gives me a chance to enter every apartment and have friendly conversations about the property and trouble spots. 

For buyers, the current environment offers the chance to negotiate better deals, particularly in areas where sellers are more motivated.

Do I take a chance on a property that may not cash flow for a few years?

I simply shook my head.Unfortunately social media has made it easy for these bad actors to get in front of their target clientele and it's normally the  clients who have no liquidity, poor credit and very low chances for success to begin with in this business and put these courses/mentorship on their credit cards who fall even further behind. 

The more of these assets the sponsor possesses the greater the chance and easier time he’ll have 1.

There's a chance that you are crapping on their grandparents' hutch or the dining room table that was in their childhood home.

Since there's a chance I might move away in about 3-4 years, I want to make sure I can rent it out later and cover all my expenses with the rental income.Can anyone recommend areas in downtown Chicago that would fit my criteria and might appreciate a bit over time?

Chances are you didn't use it when you purchased so unless something changed you should still qualify and there wouldn't be benefit to including that. 

What I am getting from the friendly leader term is, I have a better chance at getting a my project fiance through them.

We have guests there from 3 to 15 days at a time and it is way out in the boonies so there isn't much of chance at this happening.I don't agree with shorter stays causing more problems.