This is something a lot of us learned in high school when we couldn’t get the captain of the football team or head cheerleader to go to prom with us – there is a very real possibility that your tenant is just not that into you.
You cannot make a person be a great tenant by trying to be an even greater landlord. Tenants will often try to make you feel like they would have paid or done what you asked, except that since you didn’t fix that tiny drip, install the carpet they wanted, or paint the front door, they had no choice but to stiff you again. Instead of paying up, they will dangle an unwritten check in your face like a dog who must spin around before earning a treat.
Clearly, meeting your obligations to repair necessary changes will help maintain a good landlord/tenant relationship; but some tenants have a reason each and every month for why they don’t have to pay the rent. These tenants are just waiting until you finally make it a priority to boot them out. Fix the reasonable requests they make and give them one last chance to catch up. If they still make excuses, it’s time to break up and seek a new dance partner.