@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

My recommendation would be different if you were a high-income earner or if you wanted steady equity growth.

Also I have not worked out the financing yet. if I just use my cash then the Cash on Cash drops to 8 or 9% and that would be below my Cash on Cash target.Generally speaking and of course just numbers I picked out of the air for reference when running numbers in my head, I am looking for Cash on Cash greater than 15%, high probability of long term occupancy, and no expected major Capex for 2.5 years after purchase and purchase time repairs which I would add into the cash on cash evaluation before pulling the trigger.So there are some more details to be worked out in my head but being it is my first one and only learning what I could from youtube videos I thought I would get some feedback.With all that said, in my head it seems like it could be a good start.Thanks again Jaycee and Gavin for your feedback.

Some folks will give you the simple reply that if you can't fill it, your rent is either too high or something else is wrong with your ad.

I am assuming here, but if it's been on the market so long, it's priced too high for it's condition. 

I am not familiar with how HELOCs work but they declined me saying my DTI is too high.  

Seems like a high-risk, low reward situation though.

Those holiday numbers are a bit low, those daily numbers are a bit high. 

Strong rental markets with low vacancy rates are ideal for long-term holds, while areas with high ARV growth are great for flips.

Years ago I spent many months working in Indianapolis and staying at the Canal Street apartments.