Cash invested: $80,000 Acquired this property Sub-to as a quick flip with minimal repairs required.

Chicago would also require a $0 exempt stamp,Just a FYI, Any deed recorded in Chicago will require a City of Chicago water cert.Directly from my title guy.But like John said your attorney should be able to tell you exactly.

If it was me...I'd check with zoning to find out how many dwelling units I could build, and I'd find what the requirements are for those units (type of house, height and setback restrictions, etc.).Then I'd find out what local builders think the cost to construct would be - just get a cost estimate per square foot for 2 or 3 different levels of finish.

Is it required to have a brokers license or be listed under someone that does? 

This would allow me to save money compared to paying cash or the huge Down-payment DSCR loans require.

It's critically important to make sure you know the exact zoning in regards to minimum stay requirements before you go too deep into a property.

Just looking at their website,  there is no useful or helpful information that a sophisticated investor would normally require (to even give them a chance of being considered).

I can come up with only about a third of the required down payment. 

If you only have to resand the flooring and it's cheaper, maybe go with that instead,JC township will definitely require permits for plumbing, electrical, gas lines.

They usually require experience and they are lots of docs needed from architect drawings to a lot of permitting.