But is there anyone willing to share their experience if they started with my similar conditions: Already with a family, with teen age kids about to go to college in a couple years (Very Scary) It will really help.

I know on paper you can make it look like a sexy deal, but in reality, it is a tough one!

You'll be suprised (or at least I was) how many beginning teen investors are on this site.

Have you considered adding something to make it a little more "sexy" like mounting a flat screen TV to include with the unit, including an outdoor grill, or adding black-out curtains in the bedrooms? 

Ramsey is for the undisciplined.If you want to follow Dave, start investing when you're in your teens.

Not as sexy as Pilsen, Humboldt Park and West Town, but you may have better luck finding deals that meet your needs there.  

Yeah, selling a house of that price looks so sexy and enticing, but @Dell Schlabach, you hit the nail right on the head, IMO.

that needs to be cleaned many many contractor bags or even a dumsterget a teen in the neighborhood to assist with clean up if you just cant muster up the vigor to tackle the clean up but honestly it isnt so bad. clean up happens pretty quickly big items first then sweep up starting from the corners and wall edges and work in toward the center of the room.investing in a big metal dustpan and a broom that is tied together well is the key. there will be more to follow. 

Cleveland is not a sexy play etc...   

I worked for a mason in my teens and pointing materials are cheap.