I'll also ask my Enrolled Agent what his take is. 

While you may have a buyer today, you may not have an equivalent buyer (or any buyer!)

A lot of my buyers in Denver and Colorado Springs will house hack by Airbnb-ing that basement.

Specifically, I'm interested in understanding the discount buyers are typically looking for.

One thing that buyers/borrowers often don't realize is that you can also do Conventional, VA, and USDA for owner occupied property in addition to the FHA 203K product.

We purchased it the traditional way by going through an agent, we viewed some houses on our second trip out there and ended up picking one and going for it.

You'll be fine unless you want a job in real estate (like being an agent) that requires heavy outreach, cold calls, or interaction with others. 

I am new to the Chicagoland and am interested in connecting with investors, contractors, agents and lenders alike.

Having an entity does not convert payments that are non-deductible and then makes them deductible.You want to work with a CPA who understands the deductions eligible to real estate investors(and agents since your profile mentions that you are an agent). 

I am an agent and investor in the area and would be happy to talk some RE!