I'd follow JW's thought process and even consider posting a note on your neighboring doors...to let them know as a neighbor that it isn't appreciated that there is smoking inside, please kindly consider taking your smoking outside.I feel like the approach is everything here...Chicago is a weird place and hard to enforce a lot of things.  

Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: Best way to get that is by working with a real estate tax expert.

Maybe post a cliff notes version to make it easier for people to help you.

Post a notice today.

I guess my post is a little silly come to think of it as I'm taking more than 20% effectively as I take 100% of cleaning fee. 

Maybe you just need to check some box or put the numbers in a different spot.You aren't even posting here because you have an investment, right? 

I've thought about writing this post for many years.

Personally, I feel as though it was very lucrative back in the day, but it is much more difficult now to see a great return on a STR post-covid due to a saturation of people wanting to become STR owners, municipality restrictions, etc. 

From a valuation standpoint, the calculated cap rates in your original post and some of the other posts here (the 5.3 and the 6.6) are irrelevant and essentially useless.In your initial post, you mentioned the average cap rate in the area the property is located is 6.4.

Bring me short sales and owners trying to avoid foreclosures, owners needing post occupancy….additionally please reach out to me if you’re holding notes in default you need off the books!!!!