Clearly, this is normal wear and tear for such a dated setup and in such a vulnerable location.  

@Helen Robalino We find alot of poorly managed properties that can be purchased at the 1% rule and once normalized they end up being closer to 2% if not better. 

@Travis BagleyThe normal terms for commercial mortgages are 5, 7 and 10 years.

You should be able to get a feel for what is a normal number of listings and how long they stay vacant. 

The quote you have is normal.

So, I would send the Tenant notice, citing the lease clause, and give them a timeline (if not defined in the lease) for completing repairs and/or restoring the property to it's normal condition. 

Normally you lose the deposit and that’s about it…At the same time, I think taking action is a good thing.

Feel free to message me and I can frwd all the 2021 docs to keep compliant.Make sure you collect a security deposit (normally I would not recommend security deposits in chicago) as the roommates tend to just move out with no notice otherwise, even in the class A areas.

Here is an overview. https://www.reubenlaw.com/cali...I would also look into utilizing SB35 which is another state law that can get you planning approval within 60-90 days which is light speed compared to the 12 to 24 months it normally takes - or longer if there is community opposition to the project. 

Common area electric and other items I would expect to be part of the HOA fee, and those would be covered in my normal monthly bills, not billed back to the tenant directly.