IN spring of 07  I got as liquid as I could get ( not that I predicted the magnitude of the GFC) it was just rolling out of some large deals...

So it isn't just a matter of getting your license and then the money rolls in.That said, it is helpful to have.

I also couldn't tell how the roll-out worked or if it was complete. 

Setup keyword alerts for Chicago and search the forums for "Chicago roll call" to find people in your area.

My advice if you want to get paid for purchasing the property is this: 1) Roll the funding fee into the loan (yes you can do that but just make sure that the numbers still make sense) 2) Negotiate the contract so that the sellers pay for most (if not all) of the closing costs.3) Talk to your loan officer and schedule a closing date that extends your first mortgage payment out as far our as possible.

I need someone who knows the market and rents in this area and someone that doesn't mind putting in the extra effort to pull income/expenses/rent rolls/etc!

Can I sell three separate SFH in that time-frame and then roll it into an apartment complex for example?

Go thru each unit and see what needs to be done to make them rentable. is there a past rent roll?

After you will have to start your due diligence, which includes inspections, insurance research, rent rolls, lease agreements of the tenants in place, their background, proof that they pay in time, rental market analysis, comps etc...I hope I gave you a good idea of what you will have to do generally. 

In most cases that cash offer will be too low and then you roll right into the sales pitch for owner financing.