Originally posted by @Mary M.:
Tenants move. You cant stop them..... IMO you have to mitigate their damages, which usually means you must work diligently to get a new tenant. so, say they want to move at end of November - you would work really hard to rent it out for that time frame..... your locale may have specific language... or your lease may have a buy out clause... either way let them move, with good will.... there is no benefit to making it ugly.
ETA - pretty easy to find the relevant laws for Illinois "If you don’t have a legal justification to break your lease, the good news is that you may still be off the hook for paying all the rent due for the remaining lease term. This is because under Illinois law (735 Ill. Comp. Stat. § 5/9-213.1), your landlord must make reasonable efforts to re-rent your unit—no matter what your reason for leaving—rather than charge you for the total remaining rent due under the lease. So you may not have to pay much, if any additional rent, if you break your lease. You need pay only the amount of rent the landlord loses because you moved out early. This is because Illinois requires landlords to take reasonable steps to keep their losses to a minimum—or to “mitigate damages” in legal terms."
https://www.nolo.com/legal-enc...
In California you will only get the difference between the day they moved out and they day the place was rerented. It sounds like Illinois law is similar, based on the quote above. I've found those clauses nearly 100% unenforceable in real life.
This might be an unpopular response, but I'd say you're behind the curve in managing your property. Instead of griping about the past, you should have dealt with it as it came up. Let them move, charge them for what you're legally/easily able to, and get another tenant in. Negotiate a small or medium inconvenience fee for turnover costs and allowing them to break the lease. Raise your rent for the well screened new tenant and get on with things.
I wouldn't take issue with a change in payment arrangement that you're already operating upon. If you wanted an alternate arrangement, you should have set up something when they told you it was difficult to get the direct deposit. You could have done Cozy, Zelle, Xoom, Paypal, or other choices. By not working it out when it came up, you implicitly agreed to the new arrangement. Ditto for the late fees. If you'd set up a Cozy account, they would have been billed automatically for the contractual late fee, no communication from you involved. You should have taken issue with the cat when it showed up via a notice of lease violation, a new pet addendum or an increased deposit or increased monthly rent, or both. If the cat ruined the carpet, deduct it from the deposit. That's why you have a deposit.
This is a business arrangement that you're running like a friendship. You're already behind the curve as a landlord, but most of these are trivial issues and not worth rolling up your sleeves over. They're trying to work with you... you should respond accordingly. It may take a couple of months to find a place and close escrow anyway. It's unlikely they're leaving before January unless the househunting, loan and escrow glide along without a hitch.
I find more success with cooperation than conflict. Live and learn.