And it's not always smart to do the work yourself 

Jasmine he is a very smart man.

Not good enough...the woman went into a tirade calling me a Slumlord and some choice 4 letter words.

City services are largely dependent on property tax and local sales tax revenues so as these fall, cities have no choice but to cut services.

Show that you are young and smart.

DoctorEvictor.com mentioned above is a very good choice although I've never used them.

Getting involved with a partner definitely seems like a smart move for me.

I think that is very smart.

While not my first choice based on personal comfort, financially it does seem most sensible.I think I need to educate myself more on the ins and outs of renting before making a decision.

Assuming the rents cover your expenses, in 30 years when you're in your early 50s and the mortgage is paid off, and you've done the smart thing by raising the rents over the years (this is Chicago we're talking about, not Podunk, Iowa), you will be sitting on a multi-million-dollar asset that cash flows thousands of dollars per month at the cost of a measly $20k or so out-of-pocket when you were 23.