The building: asking on MLS is $400k 1980 build, 8 units, all 2 bed 1 bath Class C. 62 days on the market.I used verified rents from 2008 as well as current listed rents for the building to figure a conservative monthly rent to be at $4750.$57k gross annual return. take off 30% (8% vacancy, 12% PM, 5% Cap Ex, 5% Maint.) 

I think it's really going to depend on tenant and property class.

If it's the latter, in the mid 90's there were a gazillion homes that used wood product siding that was problematic to the point that there were class action lawsuits concerning it and many homes were resided under conditions of the settlement.

@Dwight Cook if the property is producing income it may actually be easier.

Also varies greatly on what class of homes you have / they have and the income level. 

This would be a home in a C/D class area which means that 750 is not the most stable rent to count on either. 

Are these units Class A, B or C?

There are less free lunches but if you know how to cook the food has never been better.

Looking forward to the Master’s Class next week!  

If you plan on getting into these markets, I wouldn't expect much cashflow at all but if you are able to weather that in the mid-long term game, I just don't see A class neighborhoods in Chicago going anywhere but up (both value and rent price).These downtown neighborhoods are my bread and butter and I would love to connect with you to talk further about what your plans are and what types of properties you'll be looking for.