I will say right now, it's mainly breaking even from month to month only because I have to pay my parents $125/week to transport the cars (we offer free delivery).

Just get them cheap enough to account for the renovations.

Our plan is to live here for a year or two, for very cheap, and use all of our extra cash to acquire rental properties (obviously setting aside reserves for each property).

North Shore/Barrington/Hinsdale.... those areas are not cheap and are going to cost you as much or more than living in the city.  

I have an opportunity to pick one up for cheap, but am afraid of paperwork requirements!

Please let me know if they are reasonable.Insured Closing Letter = $125Tax Certification = $20Electronic Retrieval Fee = $50Notary Fee = $45Overnight Delivery Fee = $12Incoming Wire Fee = $22Good Standing Cert for PA LLC = $40Lender's Title insurance = $50Total Settlement company fees = $364Owner's title insurance = $1154  (Sale Rate - for purchase price of $105,000)Please let me know if these charges are reasonable?

Lots of people are hesitant about that area, but the properties are still cheap, and there are LOTS of 2 and 3 unit buildings that just need lots of paint, flooring, and drywall.  

Money is still cheap so personally, I would use leverage and buy more properties than you could if you paid cash.

Income is of lesser importance as a long term game plan.So two basic scenarios...buy cheap, park cash, minimum profits, cash out before expenses eat up profits.....or invest for appreciation and ride out the zero or negative income, cash out. 

I recently did over two kitchens majority of materials came from Homedepot our cabinets uppers and lowers were dinged in delivery, I ended up getting a few free because we had alot of issues with delivery.