Legal Question in Landlord & Tenant Law in Illinois

You state no reasons for your "issues", but if he sues you, you could counterclaim whatever you think he owes you. The differences are: if you two are roommates and he can show there was a general agreement to share costs over time, he has some proof of an agreement. Since you state no reasons for your "issues" there is no way to assess whether your counterclaim would have any validity. For $200 it would be better to settle, however, since filing costs could double that amount if you lose, esp. if your counterclaim is that uncertain. But if you do settle up with him, you want a release for any other claims he may have and your housing agreement if you are done with it. Or, if you're not done with it, time to put it in writing?