There are several data points that come to mind – population growth, employment, crime rate, % owner occupied, school ratings, and proximity to desirable amenities.

Population Growth, Unemployment, Median Income, Sources for jobs etc.... any thoughts?

I’m not much more connected and knowledgeable about Chicago as I am elsewhere, alart from knowing that taxes are high, winters are brutal and population is decling every year.

I also implore you to compare the population growth/decline in the different cities.

There is strong population growth, above average yields, and properties are available for 25% to 50% of the national average.

I would guess whichever area has the highest potential population growth.  

Population Net Migration In/Out Average Home Price Rent-to-Value Ratio Local Economies/Types of Jobs Income/Property Taxes Landlord or Tenant Friendly Laws Crime Rates Schools

You don't have to run faster than the bear, you just have to run faster than your friend.Well, you are the friend, who does not make it.There are probably more than 10,000 leases signed in the greater Milwaukee market every month (my guesstimate based on population and home ownership rates), so if yours don't get rented, you have to ask yourself why not mine? 

The town is only 297 people, but that includes areas for miles around the town so it is sparsely populated.

Depending on the population growth of the city, my property manager rented my D area property out within 48 hours to Section 8 Tenants.