Should You Charge A Late Fee?

Should You Charge A Late Fee? 

The lease that I use gives my tenants a three day grace period, before being charged a late fee.  I tell my tenants that if they communicate with me and do what they say they will do, I may even be able to be a bit more flexible.  Sometimes checks can get lost, or emergencies come up, so I have at times waived the late fee. As long as it does not become a habit and does not cause the owner's distribution to be delayed. In this way I differ from a lot of managers and might be considered too soft to some. I like to consider myself fair and flexible. Some of my tenants have been renting from me for years, cutting some slack sometimes can go a long way in keeping a good relationship with them. 

I have had a couple of instances where a person started to take advantage and I quickly had to put a stop to it. I have a current tenant in a higher priced property that is late every month, and pays a large late fee and it works ok for the owner.  He has a business and sometimes has to wait for his clients to pay and he always catches up. They take awesome care of the property and are easy to work with.  Because this owner does not need the rent by a certain date to pay the mortgage, this situation works.  

I have had this same situation with owners that need the money to pay their mortgage and it didn't work.  That's why I don't believe in being inflexible or having a "blanket" type rule. Yes the late fee is due and payable after the three days, but sometimes collecting that fee, can end up costing the owner more than if we just let it go.