That looks mostly cosmetic from the photos, but I thought I saw an interior air unit so the HVAC could be shot, basement flooring is just concrete.

@Michael Dumler Thank you for your insights man, I got a few books to finish ASAP, once I am done I will execute your provided lists literally.Currently I am in Stone mountain, lakewater block.

We have had 2 houses where we removed pools, 1 was large above ground with a deck and the other was in ground with concrete around the pool. 

Other than wanting to buy another property, you would need a concrete reason for not living in the property for one year. 

I am looking to buy the ugly duck on the block that can grow equity and have stable cash flow- about $500/month.

You have to either get lucky, have an unfair advantage, or do the necessary blocking and tackling to find situations that create deals.

I want to contact the owners of tax deeds /pre foreclosure before they hit the auction block.

Do you have a concrete or wood subfloor? 

It's doable as a market to do what you want, but you must understand the block dynamics if you are going for Chicago proper.

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