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!

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 would pass on this one.A deal should be where you are buying the property cheap enough to get everything done and still have cashflow.

I only invest in either private pre-sales of pre-development properties at a substantial discount compared to their market value and launch price and rom a developer who I personally know, has a great track record and give me cheap developer financing by Mexican standards.

Sid Bogue They are very cheap so I provide them.

Generally, it's very cheap.