Brandon
Kentucky law draws a clear line between normal wear and tear and tenant caused damage. Normal aging of an older home is your responsibility. Damage caused by misuse, neglect, or refusal to follow basic maintenance instructions can legally be shifted to the tenant if your lease supports it and you can prove causation. From what you described, you potentially have three separate categories of tenant responsibility:
HVAC system damage. If a licensed HVAC professional has stated that the failure was caused by dirty filters and overheating, and your lease places responsibility on the tenant for filter changes or negligent damage, this is not normal wear and tear. Repeated failure after being warned strengthens your position.
Bathroom ceiling moisture damage. Long, unvented showers with no fan, window, or door ventilation can cross from ordinary use into misuse, especially if you provided a dehumidifier and instructions. The fact that you took reasonable steps to prevent damage is important.
Living room ceiling and paint damage from humidity. Refusing to use AC during extreme heat and allowing moisture to build up can support a claim of neglect, but this one can be harder to prove unless a professional links the damage directly to humidity and tenant behavior.
What to do before demanding payment. Your strongest move right now is documentation and formal notice, not an immediate demand for money.
I strongly recommend you take these steps in order:
Gather and organize proof: HVAC invoices and written opinions stating cause of damage, photos of filters, ceiling damage, peeling paint, and moisture, copies of written communications where you instructed her to change filters or ventilate, and a copy of the lease clause on negligence and damage.
Send a written notice to cure. In Kentucky, you can issue a written notice describing lease violations and giving the tenant a reasonable opportunity to stop the behavior. This should be calm, factual, and specific. It should state what the lease requires, what damage has occurred, what behavior must stop immediately, and that continued damage may result in charges, lease termination, or both. This notice is not a threat. It is a legal paper trail.
Require future compliance in writing. For example: filters must be changed on a set schedule, bathroom ventilation steps must be followed, and AC must be used to maintain reasonable humidity. If she refuses or continues the behavior after this notice, that becomes strong evidence of willful damage.
Recovering money for repairs. There are three realistic paths to recovery, and they are not mutually exclusive.
Charge against the security deposit. If and when the tenancy ends, Kentucky law allows you to deduct for tenant caused damage beyond normal wear and tear, provided you give an itemized statement. (KY Rev Stat § 383.595)
Demand reimbursement during the tenancy. You can send a written demand for reimbursement supported by invoices and lease language. Some tenants will pay once they see the paper trail. Some will not. (KY Rev Stat § 383.605)
Small claims court. If she refuses to pay and the damages are well documented, Jefferson District Court small claims is often the most practical option. Judges care deeply about proof and whether the landlord gave clear notice and opportunities to fix behavior.
A word about habitability and older homes. You are right to mention that the home is older. That does not excuse tenant misuse, but it does mean you must be careful not to frame this as a design defect. Focus on behavior, warnings given, and professional opinions linking that behavior to the damage.
When eviction becomes part of the conversation. If the damage continues despite notice, Kentucky law does allow termination for material lease violations. Eviction should be a last step, but repeated destruction of major systems can qualify as a serious violation if properly documented. (KY Rev Stat § 383.660)