When all the statistics show that your chance of making it out of the income quartile you are born in is very very slim.

@Nick RutkowskiI’m looking for long term tenants ( no vacation property) I was looking at the city statistics the other day and looking at things such as their poverty level as well median household income couldn’t make a fair decision I had mixed feelings about it!

I put my responses to your questions below in bold:-Do you recommend any loan officers or real estate agents in the Chicago area who have experience creating successful outcomes for people with goals similar to mine? 

Hi Patricia, This will vary market by market and neighborhood by neighborhood but you should be able to gather some market statistics from STR data collectors, talking to people on BP and local Airbnb/STR Facebook groups in your area.My market (Sacramento) has been able to consistently be in the 85-90% occupancy for Medium Term Rentals.

That's a bold assumption.

I don't want to bore anyone with the statistics unless you are interested, but we have 15% of our properties still vacant while having unprecedented need for housing in our poorer neighborhoods. 

Although the crime statistics don't paint the town in a great light, being in the city gives you an entirely different feel.

I do see the statistics are not on our side though, like crime rate, poor education and more. 

I have been trying to find existing home sales statistics for Larimer County, Colorado for hours with no success.

If you're starting out with a huge stack of cash in your pocket, then you can do bold & hold and build wealth over time.