We would like to play ball with the cash buyers in the area but are stuck looking for hard money.

Usually the "golden rule" comes into play here.

I'm well aware that the guidelines/costs for financing 5+ units is a different ball game.

Get pre approved with your lender and make a few low ball offers and get used to the negotiation process!

Ideally, we'd like to find a property in Edgewater or East Rogers Park as we love living here, but we're open-minded as we're newbies looking to get the ball rolling toward our goal of thirty properties in seven years.Thanks for your time!

Shoot me a pm with your contact information and we can get the ball rolling. 

Assuming you are dude with a 9-5, a dream, and the balls to pull the trigger on a 4plex don't waist your time and money with an LLC.  

Regardless, in this case I actually purchased this property in 2015 from a bank, so I doubt they would have wanted to play ball with an option.  

@Ramon Huerta from what the owner says she just wants it gone so I am trying to come up with a fair offer, not just a low ball, which is where i currently stand.

You might not want to hold the house longer than that.Obviously all of this takes a little bit of crystal ball future vision, which is why you should always buy right on the front end irrespective of where things are in a cycle, upturn or downturn.