Chicago 2 flats, berwyn, forest park, hermosa and ? advise please

[Dan S.]

Hi Chicago area investors. Please share your experience and insight! I'd like to get a 2-3 flat near where I live (Oak Park IL)

I have cash can wait till winter & looking at maybe REO foreclosure, Fixer, util off.

I am holding out for 140 for a 2 flat,  or under 200 for a 3 flat

Where should I look? 

Working class, not too much crime. 

I'd like to do this on Berwyn, Forest park, elmwood park, north riverside, Hermosa

Where else should I look? Cicero?

I live in oak park, and work a 9-5 so I dont want to get a place too far away

[Alex Bok]

@Dan S. those numbers are going to be a little tough to stay in your area. Unless you are looking in areas like the south or west side. Are you trying to do a house hack with FHA or conventional?

[Dan S.]

Hi Alex, Thanks for the reply. 

• Working class areas, not too much crime, like the places I mentioned. Nothing like south or west side
• I have cash,  looking at maybe REO foreclosure, Fixer, util off. Maybe something someone bought at auction and wants to flip in a quick private sale, I am trying to build contacts for that. (FHA or conventional like you suggested couldn't buy that kind of stuff. ) All cash sale is part of how I plan to find a deal
• If I look over the past year on redfin for example I see a bunch of places that sold for what I am looking to buy.. 

so the deals are out there, or at least they were.. the question is: 

1) am I looking everywhere I can be.. I need to cast a wide net

2) Am I connected to everyone I need to be? are people selling places off MLS? are there people who flip auction sales (I wont buy without going inside a place) for cash that I can connect with?

[Hope N.]

You might be able to find those numbers in Cicero or Little Village. But personally I'd pay a little more, take out a loan, and that will open up other neighborhoods for you.

[Dan S.]

Hi Hope, thank you for your response! Would you be kind enough to share more on your opinion and experience and why you might stay away from Cicero? 

I am almost definitely going to get a 5 unit in Cicero, and if you have reasons I should be wary I would like to know them. At the very least I want to go into this thing with my eyes open. Thank you in advance!

[Jeff Burdick]

Welcome Dan!  I'm a fellow investor on the north side of the city. There are many great neighborhoods with good cash flow and potential for appreciation. What sort of price range are you looking at?  

Also, just my opinion, but since you work full time, I strongly recommend using a property manager. I tried to self manage at first while working full time and it was a challenge.  

PM me if you'd like to discuss further.