Taxes are reasonable (in most areas), and there is a significant lack of quality affordable housing.  

Check with an architect first to be sure you can fit your vision into the existing lot, as it's zoned currently.

I am looking at different loan options but to break even (not having to put any money of my own in the house after the initial down payment) the current down payment required is that much. 

@Parker BullardFrom my experience, house hacking is a great way to reduce housing costs by renting out part of a property, like a duplex or triplex.

House hacking, if you will. 

If you walked into a bank, your pre-approval would likely never qualify for a house hack duplex.Did they count 75% of the expected rent towards your DTI? 

As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

In other words, I can afford the house with or without tenants. 

My friend is selling his house and is open to an assumable mortgage.

Sounds like you should go the house hack/FHA route.