@Zachary Giles Hi Zachary, I think Joe nailed it on the head.

Boulder County (not in the city or towns) also allows non-owner-occ STR, but with a cap on the number of nights per year it can be rented. 

Account Closed nailed it too -- you'll be refinishing floors when they move out if its hardwood.

Looks like @Samuel Pavlovcik nailed the situation spot on.Keep us updated on how it works when you send it back through the Chicago building department.

My question is what are the things I should pay attention to and really nail in order to have my listing stand out\ make my listing the first choice when people visit the area? 

I agree; Nailing down the best possible screening process as soon as possible is probably the top priority. 

Is there a cap on the interest rate of your mortgage?

That leaves me with option 4 which would be very cost effective and relatively simple to do...cut the planks to the correct size, find the joists with a stud finder, and nail them up after applying an adhesive to them as well. 

Sometimes when it looks like a deal, but can't make it stick, we can nail it. 

@Jared Smith you've nailed the first part of the due diligence phase!