Next time it may not.  

A team - I have been bitten too many times, relying on one cleaner, so every place I hire has to be able to provide at least 2 cleaners in case there is an issue for 1 on a turnover day. 4.

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?

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.). 

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!

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

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

I have to try something that would allow me to make money online because my currency is $7 to $1 US and the key a lot of the time is speed.