If not, how do you plan to eat between now and when you make your first transaction?

Otherwise the carrying costs eat up the profits.  

I'm sure my water bill and trash and P Tax will go up too, eating into my profits...Again, maybe I'm wrong, but I'm thinking at some point the pendulum will swing back a little towards reasonable.

Don't want to have to eat the cost of a foreclosure. 

From what I hear, it's quite the hot market in Chicago and you may end up spending a significant chunk of time so you may only have to find a subletter or you may just have to eat it for a bit.

Not sure how you manage to do both.I realize now that I may not be able to have my hypothetical cake and ethically eat it too.

You will have repair costs, and they can eat you alive.

From my experience, a person's standard of living is higher when there is extra money each month rather then having a little nest egg (the rental) gaining equity that can be used at a later date.

My fear is that I will need to put more money into the house (i.e. water heater, furnace/ac, etc) that will eat up any kind of profit that I might have.So, finally, a couple of questions.

However, paying for heating and those crazy property taxes would eat most/all of that up in your case.The tax situation would make me think twice about investing in 4plexes in your area, period.