Also seems like it's dominated by HOA, but not sure.

I would HIGHLY recommend you stay away from condo's, townhouses or anything with HOA's.

Between price to rent ratios and HOA/condo fees it can be tough.

There are mandatory HOAs.  

If a business owns a property you are interested in, this can help you figure out who is the wizard behind the curtain (to use a Wizard of Oz metaphor).HOA COVENANTSIf the property is in a subdivision with a homeowners association or condo association, the HOA can set additional rules about what you can do with the property.

Would appreciate receiving allAnalysis question:Property: SFR Year Built: 2003 State: GA Purchase : $48K Rehab: $3K Status: Vacant Expected Rent: $925 HOA: $150 pm Insce: $60 pm Tax: $60 pm Repairs allowance: $100 pm Vacancy %: Estimated at 15% Price History: Sold Mar 2006: $128K Sold Aug 2013: $39K Sold Jan 2014: $48K Averaged Price Estimate from 4 realty sites: $55K, Question: Have Offer from a Realtor to Buy property at $62K with Seller (me) financing Realtor will be asking for 3% commission for selling property, possibly towards down payment, so net say $60K (I'll make Buyer pay for other misc chgs and fees) What would be breakeven interest rate to make comparable the 2 options i)the rental versus 2) seller financed sale at $60K with $6K down and $54K financed?

Or a $15k condo that rents for $600 a month (subtract HOA dues from that formula, so if the HOA dues are $150 then you'd really be at $450 a month gross before repairs).- Finding deals?

The mortgage is up to date, no liens, and HOA fees are up to date (so he says).

The only other property I was considering was a 2 bed/2 bath condo for 105K with a 110/month HOA. 

At first glance  seems like the Chicago market is saturated and every single property has an HOA fee which I've heard to stay away from.