You should be familiar with Fair Housing, Landlord Tenant Laws, and how to effectively perform a lease-walk (i.e. showing).

It tells me you probably had a very effective ad with good pictures, and that the property is nicer than most the rentals you are competing with in that neighborhood.  

Lot's of development coming to the area of my new property, but it won't start effecting the demographics for at least 3-5 years. 

Rent Income:  $167,940 Less: Vacancy/Deductions:  $16,794 Effective Gross Income: $151,146Less: Expenses:  $81,727 Net Operating Income: $69,419Less: Debt service: $31,920Total cash flow:  $37,499

I'm looking for the most effective strategy on determine renter costs owed upon move out :On top of that I would like advice on my current move out situation :Renter put his 30 day notice in Sep 1st so we started showings right away.

The actual age isn't as important as the effective age. 

Does anyone have an efficient and effective system they use when previewing a property? 

If you effectively use the discounts you can often pay for the membership with those alone.Go to the Oct meeting and just pay at the door.  

On December 12, 2013, the Circuit Court of Cook County entered general order 2013-07 effectively stopping the Cook County Sheriff from enforcing eviction possession orders.

To do that effectively you probably need to learn enough to manage them yourself.