Chicago vs Milwaukee Multifamily?

[Jonathan Seyfert]

Hey BiggerPockets community,

I am looking for some advice on location with regards to starting my investment career. I will be looking for multifamily properties ranging in price from $300-$500k in better parts of town with the intent to buy and hold. I, like many others, preferentially value cash flow over the other ways I can build wealth through real estate. I hope to make this my niche and just wanted to see if there were any opinions on location. 

I plan to use property management companies, but like the idea of being able to drive back and forth to a property within a day. I live in the Northern suburbs of Chicago, equidistant from the two cities, hence my interest in Milwaukee and Chicago.

Have been researching Rogers Park, Jefferson Park, Edgewater, Andersonville in Chicago and East Side, Brady Street, Downer Woods in Milwaukee. Can be flexible on the upper end of my price range if the rent to market value ratio and/or number of units were in my favor.

Any thoughts would be greatly appreciated on these cities or anything in between! 

Jonathan