I suggest talking to a local broker, there are many reasons I set up a brokerage instead of continuing to manage a team inside of a bank or "direct lender", but mostly it comes down to being able to offer better rates/fees, a more diverse product line, and ensuring more control over the process because I can take my business elsewhere if underwriting turn times hit the ceiling or other service issues arise. 

Stay diverse in asset type.Finally, as one of the above posters mentioned...

Look for things like population growth trends, diverse economies and price/rent ratios.

With 6 units, there is more diversity in the rent roll.

I’m looking to build a network of like minded people with diverse backgrounds and specialties in the REI community.

Chicago is too large and diverse a market to answer your question without you answering some questions first:  Do you want to hold, flip, are you investing in cash, leveraging, how much risk are you willing to take, do you want to live in the property, do you want to invest in the burbs or the city .....   

@Calvin Smith Lol yeah my market is very diverse from very wealthy vacation beach homes on the ocean to huge farmhouse estates to very low income inner city areas so I will definitely keep this in mind based on my clientele

Milwaukee is a very diverse market place - you go from the 1920s built and upscale East side with a lot of $1500+ rents to a rather rough inner city ($600 to $1000) with several troubled areas to relativley quiet 1960's urban areas within minutes ($1200 ish) - which is of course an over-simplification of the city's complexity.

@Michael FucilloIf you are buying with 30 year fixed rate debt at a low interest, in an area with a diverse job market and growing what risk could there be?

Residential real estate that doesn't consume more than 1/3 of the median household income in well-located cities with diverse economies and generally temperate climates will always be in demand.