Talk with a few realtors in your area and get their perspective. 

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

The SEC claims Fossum misappropriated hundreds of thousands of dollars from the funds by living rent-free in a fund-owned home and having the funds pay for extensive international travel and his federal taxes.

I love talking shop!!

The property listed for 200k, so we talked them down to 190k and they are covering 2k of down payment.

Neal Bawa sounds like he knows what he's talking about, but his track record is terrible.

Instead of paying off the old loan and netting the rest, you talk to the first seller who you've been paying for a year and get permission to substitute collateral. 

Thank you all who responded, I plan on spending some time driving the neighborhood and talking to anyone at the local coffee shop who will talk to me.