Yeah the IL property taxes are one of the biggest downsides of buying in Illinois.

it seems like a confluence of factors have made it difficult to get started - there is lots of competition for deals, both on and off market; money is expensive; the trades are booked up forever; etc. 

However, I know this will be very difficult to pull off and is a high risk, especially since I'm already using a lot of time for my full time job and building up my insurance agency on the side after work.

While corporations must adhere to annual meetings, board of directors, minutes, bylaws, corporate officers, and franchise tax filings/public information reports, LLC’s have only Articles of Organization and Operating Agreement.  

Doesn't seem to be a consensus on here on how to write the lease up.

Often they will tell you what they're having a challenge with (like finding off market deals, a reliable property manager, etc). 

If you want to block it off, I'd do something similar to your diagram on the bottom left where the door to the new bedroom is closer to the bathroom. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Because of its proximity to the Common and downtown, it could easily get $200 a night in the off season, and $1,200 during September and October.Very long winded, but all that is to say, we’ve done a lot of planning and research, and now we’re exploring how to actually set this in motion.

@Carlos PtriawanDid you section off the basement or something similar?