As for buying single unit apartments and renting them, the property taxes again eat away on any monthly cash flow.  

Come eat at restaurant at 3101 Sutherland Ave.

Hi,Michael LeeThank you for your words.I hope you will be better soon.Probably your doctor is giving ypu half aspirine per day,but try to do sone exercice when you can,a short walk,etc...Try to eat more vegetablesCut all processed foods,rice,paste,bread,etc...try meditation or yoga...relax...your body is trying to tell u something...Best wishes,Americo

Not much discretionary income to eat out on a frequent basis.

Eat cheap and stay out of restaurants, coffee houses, movie theaters and restaurants unless its your 3rd job.  

While we really strive to be disciplined and live a minimalistic lifestyle (drive used cars/no cable/don't eat out frequently etc); our pickle is that if we are going to have to pay in the $1300-$1500 range anyways...is there much difference (of course we don't need high luxury at this point either) And yes I'm sure we could find something tiny, dirt cheap w green countertops and pink bathrooms; as my wife is a stay at home mom, I just don't want her to have to hate the place where she spends a majority of her time w our children. 

I guess I really wanted to know if there was a way of having my cake and eating it to.

and you have everything you started with, $10k extra, and a rental.Unless rent in the area is crap it sounds like you can have your cake and eat it too.

The fees crept up every year eventually eating into his cash flow.

Chicago one of my most favorite cities to visit and eat.