Update as of 10/8/2017
I didn't realize it's been almost a year since I last posted. It's been an especially tough year in the market in Chicago. There just hasn't been that many multi family properties that make sense. If/when one does come up, it usually goes within a week and goes substantially over in price. Most of the properties have gone over list price - to give you an idea, I put in a bid of $25,000 over list price and was outbid with an all cash offer.
I also had an offer accepted on a home which was very exciting! I was getting everything in order going through all the inspections and the inspector mentioned that I should get a structural engineer to look at the property, not looking good at this point. As I was in the crawl space with the engineer, he says "this is good" so I'm thinking Great!, he goes on "well, not for you, but I've never seen anything like this so it's a good story for me" and went on to describe how the foundation is in really ****** condition and parts of the foundation had shims to support it. Anyways, at this point I knew I couldn't move forward with the property. It was unfortunate but obviously I'm glad I found out before I moved forward with the purchase.
So where am I now? I'm still looking for my first property. I was really hoping to have purchased two properties in 2017 but I have to keep in mind that real estate is a long term goal, and it's always better to wait for a good deal than hop into a bad deal. With that being said, I'm starting to lower my requirements for cash flow in Chicago. I want to purchase 2-3 multi family buildings in Chicago (9-10 units) and start building equity as quickly as possible. Once I do that, I'd like to use that equity (plus additional savings) to purchase multifamily in lower cost MW cities.
Also, I'll try to update this a bit more.