The only difference I'm noticing is that a lot of the larger complexes are offering move-in specials like one month free or first month at a reduced cost of 25%-33% of the normal rate.

I am an agent, so the commission rate as reduced.

Live in that one for a year or so, still letting the tenant substantially reduce your living expenses.  

Since it was my first deal, I sought out for something that was less labor-intensive with regards to rehabbing.

At the edge of Chicago Metro.. it couldn't simply be a stale mate.. buyers and seller are just waiting it out For now, it does appear to just be a waiting game. prices have not really been reduced and, im not a realtor, but as an investor, I get sent the listings and they dont seem to be increasing in volume...but how long can a stalemate like that last before it affects values?

Rent is reduced 20% or more?

-I got a letter from her employer on 3/31, saying she is employed but hours have been reduced.  

The housing here is much much more expensive than other areas of the midwest and the older housing often has the issues that Todd mentioned above, plus the cost of labor for fixing problems is high.

You don't want to get into a situation where the tenant says the owner agreed to reduce rent or says they have a higher security deposit than the lease says.

If not, you not only have no obligation to reduce rent for him, but also calling this out states that he is not maintaining the apartment.