Update as of 6/18/18
5 months or so into owning my property and I couldn't be happier! I took over the building with only 1 tenant in place and was able to quickly find a great tenant! I was tempted to take a couple less than stellar tenants because I wanted to fill the place quickly but ultimately waiting an extra 3 weeks really saved me a ton of headaches. I started to print a 1 page info sheet listing rent, parking, info about the unit, etc. It really helped me be consistent as I realized I was answering tenant's questions differently (how much is the garage?, etc).
I'm also in the process of updating the basement so I could get that rented out as well. This process has taken me WAY longer than I expected - although I think it's just naivete on my part thinking I could rehab a basement in 1.5 months myself. The renovations include installing an egress window, installing allure flooring, new kitchen, paint job, trim, etc. I'm hoping I can finish this to get it rented by August 1st. We'll see how this progresses. I'll add pictures soon.
In terms of issues, just today I had to call a plumber for the first time. Other than that, I've had small leaks here and there but nothing too bothersome. I'm really excited to get the renovations done and will start looking for property #2 soon... although the Chicago market is pretty tight right now.