Q: Can a former landlord sue for damages if he didn't notify as per required under the contract, hence then there are none?

A: Question: "If I win as per the terms of our contract (no proper notification,, no communication until way way later, no nothing) do the damages still exist then to sue me later?"

There's a few things going on with your question and some assumptions that I need to make in order to tailor it. Let me start with the assumptions: (1) You have a claim against Landlord; (2) Landlord shows up to small claims and disputes the claim; (3) you win final judgment in your favor in small claims based on a breach of contract (your lease with landlord).

To answer your question under these assumptions, you need to understand that small claims is a lower-level trial court with rights to appeal to Circuit Court. If you were to win final judgment in small claims, Landlord cannot bring another small claims action against you on the basis of "res judicata" barring such additional claims where final judgment has been issued on the same occurrence, transaction, etc. However, this does not bar the Landlord from either disputing the claim in small claims and attempting to get an award there or appealing the final judgment to the circuit court. Such an appeal is heard "de novo," meaning that the circuit court will hear the case as from the beginning and not as a review of the small claims court. The Landlord at this stage could again attempt to defend or carry forward their claims to this court on those damages.

A: It sounds like the landlord breached the contract by not allowing you a walk through and not providing you with an accounting/itemization of the damages to the premises within 30 days after you returned possession of the premises to the landlord. You can makes these claims in small claims court. The landlord will be required to make any and all counterclaims at that proceeding or any other claims will be deemed adjudicated.