I talk with investors all the time that have been waiting up to 2 years to get their property.  

You have the area experience and data to help you, but courthouse steps auctions are blind bidding (other than what you can find through the windows), all cash, 10 percent down at the time of close, and not always clear on all of the liens associated with the house (tax liens, HOA liens, utility liens, etc.). 

We self-managed 20 properties while working 2 full time corporate jobs pretty easily.  

Since there's a chance I might move away in about 3-4 years, I want to make sure I can rent it out later and cover all my expenses with the rental income.Can anyone recommend areas in downtown Chicago that would fit my criteria and might appreciate a bit over time?

If you bought the home yourself, with a higher rate at the time, and nothing else has changed (income, new debts, FICO drop) then you may be able to refinance just fine by yourself.

Appreciate everyone's time!

The company's transformation efforts reflect broader shifts in the retail landscape, where traditional department stores are shrinking their footprints to adapt to changing consumer preferences.

Time and Money.

I currently have ~20k saved and will have more upon the time I buy.The houses in my area are around 300-350k range. 

Government subpoenas can be and are declared invalid by courts all the time.