Landlording is a business. In 2014, I sold a commercial property and needed to find 1031 exchange possibilities. What I learned in talking to potential sellers is that very few ran their properties like a business.
I bought 10 properties in a short period of time. I knew immediately that a couple tenants would need to leave. I gave one Tenant $300 cash for keys. The other I went through the legal process. Now, I’m very particular (legally) about who I accept. Included in my move-in package is a sample eviction notice which they must initial. The new tenant and I usually have a little laugh, but I tell them that if they don’t pay by the 5th the notice will be on their front door on the 6th … so don’t call yelling and asking what it is! This is as much psychological as anything. Now, I rarely have a late pay. If I do, the late payment is included … no questions asked. Hey, that’s how large apartment complexes are managed. Us small guys have a business too. Sad stories don’t work with me, “my car’s transmission is out” doesn’t work. I’m not their bank but I am very fair and equal to all tenants. Unit repairs are usually made within 24 hours if possible and landscaping kept in “I love my place” condition. I even try to get HVAC units repaired on the weekend if weather is miserable. I want the type tenant who respects property and pays rent on time.
I’m guessing you’ve gone so far with this tenant that you may need a new one to get away from the frustrations you mentioned, but that’s your call. Oh, and I only except payments via direct deposit as a policy for new tenants. So, I don’t deal with the “I mailed it last week” either. Lastly, it's best to keep the landlord-tenant relationship on a cordial business -like relationship. That’s my best advice.