They laughed their a**es off at the inspectors office when I mentioned the address.Love the specifics of the area you mention, the stories you tell and I can imagine the stories you haven't :) .I think you'll agree though, with a "recent" conversion unless there is documentation of being a legal (somehow) two family, workarounds are just that, and will leave him vulnerable to all kinds of selective enforcement.

What is the complete list of documents that I have to bring in Cook County record office?

The commercial property would be for me relocating an office, and it would be like a house hack, where the income from the rented house would pay for most of the mortgage on both properties. 

We tried calling other banks but being at the end of the year most people were out of office so we are taking that as a sign to not get it.

I am interested in buying a commercial property (office, retail) and was wondering at what point I receive information on income and expenses such as rent roll, leases, maintenance cost to calculate NOI and cap rates.

Feel free to DM me for suggestions for some good local loan officers. 

@Joshua PoitrasYour profile indicates that you are an agent, you likely want to work with a CPA who understands deductions available to real estate agents.MLS Access fees, E&O insurance, Home office, Mileage are some of the deductions available to agents.Below are some tips to find a Local CPA that specializes in real estate1) Attend a Local REIA / Real Estate meetup and see who other investors are using as a CPA2) Network with other investors from your City/State that you find on bigger pockets and see who they use as a CPA3) Look for CPA's with good google/yelp reviews where 'real estate' is mentioned in the review.4) Verify that your CPA is licensed.

Before I even got to talk to loan officer, he emailed me that he saw the fee and removed it.

@Chris Utter If your issues are you don't want to drive and you do not want her knowing your address then just get a PO box from your local post office.

HUD would consider an office or living room as a bedroom for occupancy purposes per the Keating Memo.