She informed me on December 1st that she was expecting a job offer requiring a January move-out, which she received on December 12th.

With broad, high-level criteria, you may be able to easily cross of a number of neighborhoods where the numbers simply do not make sense (assuming you already have your buy box nailed down).

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? 

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.

Each class you need to take is based on the required knowledge for the next class(s). 

Simply be a calm stand off landlord who is expecting his tenants to honor the lease - Not you accommodate their personal situation.

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