Additional expenses include: $600 yearly insurance, $30 HOA, and $100 monthly management fees.

Something to think about if you don't mind the expense of holding an active license.As far as going directly to the listing agents - while they may push for you don't assume they are all getting "double commissions" as the other poster stated.  

I make about 2600 a month and have exactly half of what I could calculate in expenses.

The houses in central Il are not very expensive compared to other parts of the country, property taxes are crazy high though. 

Understanding the difference between an "expense and a cost" is critical, and the difference between "getting there first, and getting what's left".

Chicago's market is very expensive (for me at least) and my girlfriend has very expensive taste as well so the cheapest place i have found was 800k for a 4-plex. 

The appraisal shows Reconstructed Income and Expense for the income approach of the appraisal.  

Add a pop up vent behind the stove and hope tenants use it ( In my opinion not likely and pop ups are very expensive)3.

Austin is just getting too expensive and a huge bidding war on purchasing properties so I am interested in learning more about the San Antonio area which looks promising.

There has to be enough money after expenses to pay all your bills including your loan.3.