If you will be financing this purchase, I recommend starting with a prequalification as they will really help you focus on what markets will serve your budget best.

I would recommend that you focus on which area you want to eventually settle down in.

I recommend speaking with @Denver McClure to see what is available given your situation.

I'd recommend looking at costs. your build cost is going to be well over other homes because of the fixed costs like slab, Hvac, roof, etc. check the market drivers and weight the benefits of short term versus long term. long term is no furniture and help pays mortgage but at this size it doesn't really cover everything. we didn't find a lot of economies of scale in single family detached. can you build more than one unit?

It is possible to utilize low down payment loans and live in great neighborhoods in Chicago Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I would recommend house hacking unless you had plans to move out of state.

I don't know if that is included in the total rent numbers the owner supplied. 

If anyone has recommendations for what they've been using and like, we would appreciate it greatly as well as any tips you may have for us!

To answer your question I would highly recommend shopping around on the BP online bookstore and finding a couple of books that stand out to you.

@Max Briggs I would recommend checking out the landlord resources tab on BiggerPockets.