Hi Veronica!
I can't speak to any Chicago-area specifics because I don't live there myself, but I wanted to give you some ideas of what to do to prep for a coffee meeting with someone who does.
- Pick 2-3 suburbs you are interested in- make a list of reasons why you think these would be good places to invest.
- Research for current market rent for various bed/bath combinations.
- Find 2-3 SF or duplexes in each area on Zillow, Trulia, etc. Compare the market rent to the amount of money needed to cover the mortgage and/or creative financing payments.
-Other things to consider: there should be quite a bit of money available after paying the mortgage/creative financing to cover repairs, vacancy, saving for expensive items like a roof, and maybe property management if you're not managing it yourself. If there isn't an additional $250-$350/month at minimum, it's going to be hard to cover any unexpected repairs (the number might be different in your area).
- In looking at some properties before you meet, you might find a great deal, in which case you have an excellent conversation starter with a potential partner.
This should give you some options to present to someone who is more experienced so they can answer some questions you've encountered, and you can start to zero in on the best areas to invest for a return, even if you don't find a perfect property right away.
Hope this helps!