@Jacci Konkle Hi Jacci! Wow thank you for such a detailed response :) We share similar experiences so this is both comforting and motivating.
I agree with your advice very much. I can also appreciate the fact that you moved to an expensive city, yet managed to purchase your first rental in Wisconsin. It gives me hope that I can too.
As much as I would like to live in one and rent the other, I don't plan to move back until a year or so. With that said, there is something about buying in Chicago for my first time, that I have mixed feelings about. It's just my gut. I prefer smaller towns,with a good market of course. Also,as you mentioned, I have a strong network in Appleton in the event something goes wrong etc. Similar to your situation at the time.
So, essentially you moved to Chicago and purchased a duplex in Darboy then,correct? Would you mind me asking the steps you took? I understand the basics but since you actually did it, I was really hoping you could briefly give me some advice on getting started considering my credit is decent, I have the downpayment and drive to pursue my own property.