Tenant-friendly county: tenant refuses to accept charges to security deposit

[Janna Afanasjeva]

Husband and I have been renting 1 property for the past 3 years (and learning a lot from the experience). The property is located in Cook County Illinois (Chicago suburbs), and we have issues with the most recent tenant. The property is primarily managed through a property management company (but we are heavily involved and would like to stay this way). 

Background: Tenant is refusing damage costs applied against security deposit - primarily damage costs to wooden floors and costs associated with cleaning. The wooden floors were last refinished in 2020 (have all receipts), last tenant move out in 2022 with no issues to the floor (have pictures from move-out inspection),  2023 move out - large parts of the wooden floor are covered in black chemical residue (maybe from cheap rugs?) that cannot be cleaned plus heavy scratching in certain areas plus small water damage (have pictures of all). Due to the damage to the floors, we were forced to refinish them (and basically had to refinish all floors throughout the house). We are charging the tenants for water damage repair and refinishing floor square footage that was damaged by them. The property was also not cleaned, and we had to pay for a 2-day cleaning service. We are even charging less for cleaning because the property management did not agree with our receipt and costs for cleaning. For cleaning, we have some pictures of dirt and grime but not all pictures. We have all the receipts and even maps for square footage justification. The tenant refusing the charges and threatens to take us to a small claims court. Overall, we are speaking about 2k here. 

What are our options?

I am basically stuck at these scenarios:

1. Get private legal counsel and go to a small claims court with hopes of winning the case since we have the documentation (but would cost us more if we loose the case);

2. Attempt to negotiate (eg reducing the square footage of damages, reducing cleaning fee further) but would need negotiate via our property management company;

3. Do nothing and eat the costs (this is what our property management company [and their legal counsel or so they say] is advising because we are in a tenant-friendly county). 

What would you do in our situation?