July of 2017 I purchased my first home using the VA home loan benefit for $218,000.4 bedroom/2 bath. 

In Texas, the law for example is 3 adults per bedroom.

@Bobby Narinov I can comment on the Burnham street, really if the 4800 block is North of Laskey Ave then unless you have a 1 bedroom house it should be renting very well.

@Michael Temple So a couple things 1) I just turned over the property over to PM, they wanted to rent at 1200 but because everything inside is brand new I'm making them rent at $1400 to start.  2) The house though not huge is a 4 bedroom house, and there is a premium for 4 bedrooms as there are very few on the market. 

They're using cash, private lenders, and creative financing.

It's January in Chicago and we're trying to rent out a 2 bedroom, 1 bath located in the Logan Square/Avondale neighborhood.

I have this idea that I will buy a 2-3 Bedroom town home while I am over there for grad school and live in it and rent the extra rooms out to help may the mortgage. 

We won’t show a house to a SEC 8 tenant who doesn’t have their paperwork yet for the exact reasons you stated. 1) Timing.  2) We need to confirm they have the right bedroom size and income to ensure they will qualify for our rent amount.  

I feel I have a creative mindset to work in the currently tighter market.

The home is now 1856 square feet, 3 bedroom, and 1 and 3/4 bath, with a large carport and workshop added on as well.