@Arturo Colmenero you could try referencing zoning maps to look for multi family pockets but your best bet would be to subscribe to a service like Reonomy for example if you’re serious about finding multi family properties

Hi @Zach Schnoebelen, welcome to Chicago :) My suggestion is Berwyn - it's a suburb on the near southwest side that is still serviced by our commuter train, the Metra, which can take you downtown in <30 minutes.

I just found someone, who looks reliable and I’m happy with the estimate (half of what my realtor’s flooring guy quote was).

All they normally have to do is prove that they are not the ones that are servicing the loan anymore which would be similar to a rental property, however they should not say that it is a rental property.

Thank you for your service...What exactly are you initially thinking about doing?

I'm thinking:  recent law updates, handling specific tenant issues, when to raise the rent,  service/companion animals, vs pets;    Specific ideas would be best.   

I know many say it’s too much of a hassle but I was an on-site leasing agent before for a 12 floor apartment building across from a large college so I have had SOME experience with it.I’m currently a single federal employee hoping to cut some expenses and do more in real estate.

What are the must haves and what would be a nice little extra service?

There is another house for rent on my same street that is the same floor plan and its been vacant for at least 2 months.

It's already the 4th geekiest city in the country with all of the smart people working for NASA & the private sector engineers servicing NASA.