Bonus Q: Any recommendations on solid areas in Chicago area to invest in rental properties?

The point of rental investing is capitalize on cash flow, with the chance of appreciation being an awesome bonus (meaning, investments aren't typically based solely on appreciation potential since you can't predict it, but if you can maximize the chance by investing in B/B+ props or above then all the better).That being said, most (not all) rental investments aren't made in new props.

Added bonus: it makes it easier to pinpoint leaks in the system.

Bonus income enclosed paved outdoor storage space.   

That way if all three units are rented out at the same time, I would be able to completely collect from the third unit during the given time frame, almost like an added bonus gift. 

I'm managing my expectations so that any rent increase is a bonus to my ROI and I don't cry over a broken hot water heater.

(damage bills so far total$16,000 for demolitions,etc BEFORE REPAIRS EVEN START for new carpet in bonus room above garage , new insulation, new drywall, paint ,too much to list..SO MY QUESTION ISwhat kind of insurance does my property manager carry (i hope they have it) that i can sue them for damages not covered by my homeowners rental dwelling policy???

A bonus is you can lower your expenses on the sale.

In the meantime are you taking advantage of the currently available 100% bonus depreciation?

Some mocked up info on the property, located at 5 Arnold ave in Somerville MA Top floor, renovated, open concept Off-Street Parking Private rear deck overlooking large shared yard Private laundry and storage in basement (half of basement) Low condo fee: $120Deep condo reserves and 100% owner occupied (financing is easy) Very bright and sunny unitGreat sized bedroom with bonus office/sunroom Open concept with well-defined spaces for living, kitchen, diningCertified Deleaded (no worries if you have a kid someday) Have folks done FSBO before?