@Will Almand, I would argue quads are always going to be in high demand.  

I would be patient in general and not slash prices.

Zillow and online county property records for sale prices.   

Some attorneys now specialize in these.

There is a great group of us who invest in the NL area if your looking for some folks to connect with.Now to your question, you'll find rent prices vary quite a bit in NL depending on what area of NL, but I'd be happy to give you our averages.1, 2, 3 would average $1150, $1300 and $1500. 

I am looking at first and last to move in and when the renter sells their current house, they want to put money down towards an option to buy.

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville. 

The skill comes in sourcing deals that arent only on the MLS.

I'm not not interested in regular old notes :) But, I do like partials (I've done a few others).

These people are built to value add deals, you would have to look hard for these people in your market and probably pay them top end pricing to get your properties performing amazingly well!