Hello,My husband and I are new to the site and have just put in an offer on a 3-flat(owner occupied) property for $329,000.  

On a super flat lot not in a flood zone, this is probably ok. 

Flat roofs are always a headache...just a master of when.  

We are now preparing to buy our first 3-flat in Chicago.  

Flat $200 to $225 a week.

Install landscaping that requires less water.Gadgets that help prevent water damage if water goes where it shouldn't be going: water alarms (place under kitchen sink, next to hot water heater, next to washing machine) and a "dwip" pan for under the dishwasher (if the dishwasher starts to leak, it forces the water away from the back of the cabinet and out onto the kitchen floor where it can be seen.)This is how we do it:Utilities that are variable (cost tied to use) - electricity, natural gas, and water/sewer - tenant paysUtilities that are fixed (flat fee) - garbage/recycling, yard debris - landlord pays (but we factor the cost into the rent.)In our city, both water/sewer and garbage/recycling will become a lien on the property if it is not paid.  

We learned that there are several things in need of maintenance that we were previously not aware of.I am putting down 20%.4.375% on 30yrs for a 321,000 3-flat property.

I don't know if it's out of control yet, but jobs, population demographics etc don't support the housing prices in that area.Who knows it might balloon up for a few more years and flat line.

My advice as a real estate attorney, find a real estate attorney to draft a decent residential lease at a flat rate.

@Mike Giudici  @Chris Winterhalter I just got some bids on a flat roof.