But yes, there could be a more serious underlying issue.

Thank you so much Cassi, This was my first post and I could not have imagined a more informative reply.Thanks so much again 

I’m wondering if anyone has knowledge about this area and if any developments are planned, which could make this a more attractive investment?

I recommend you find a realtor who works primarily with investors (buyers do not pay commissions so it will cost you nothing) to come up with a more targeted and winning strategy. 

I'm thinking of asking 3 - 4 contractors to give me an estimate based inspection report and then pay 2 of them to come onsite and have the specialists loook at it and get a more accurate estimate I can use to negotiate with seller. 

Considering that the housing market has undergone dramatic changes since 2008, a more appropriate question would be "What is the cheapest house you bought in the past 12 months?"

Hoping to test the waters with a more experienced partner.

A more typical ratio for condo investment would be $200k that rents $1600 this is readily available in the South Loop and largely bought by out of state investors.

To say we are a little bit anxious would be an understatement but we are looking forward to learning and growing as we continue to create a more secure future for ourselves and our two sons. 

A more advanced thing would be to schedule showings in messenger.