Future goals include expansion into Duluth, MN and the Southwest US. 

Southwest Michigan is booming.

I am also in the southwest burbs just 30 minutes east of you.I suggest you listen to all the podcasts of Chicago folks starting with mine - http://Biggerpockets.com/show65You can also learn how I buy houses every week here on BIggerpockets as I update "BP Nation" on what happens in my real estate business every single week:The Real Life of a Real Estate InvestorLet me know if you need any help.

Before singing anything I would highly recommend to visit down here and see it for your self what you are getting into.The Southwest Airline Hub is located right here, at BWI (Baltimore Airport) if you catch them on a good day you can fly here probably for about $200 round trip.     

I honestly wanted to flip and move into the south/southwest Florida market as its pretty hot right now.

Maybe consider putting the stairs to that unit in the southwest corner with an odd shaped landing/switch back and pushing your powder room/laundry to the west and then shoving your kitchen against the north wall.

@Anastasia Bourdon That's great that you are house hacking in Harvey Park, I currently have one over in College View, and southwest Denver is a upcoming area, especially Harvey Park. 

I envisioned that prices in Pittsburgh will come up and eventually level with the other southwest Atlanta beltline neighborhoods, especially if and when most of the properties and parcels along University are developed and University Avenue complete streets project is completed.  

I now reside in the Southwest Suburbs of Chicago.

Southwest PA Investors Group.