Contacting tenants before late charges kick in?

[Adam Craig]

Our rent is due on the 1st and we offer a 3 day grace period. After 3 days a $25 late fee is applied and $10/day after that.

We recently switched off our property manager and we are managing all 32 properties in house. Since then, I have been emailing any tenants that have not paid by the 3rd just giving them a friendly reminder that rent is due or a late fee will be applied.

My question - Is this too proactive? Its only 2-4 tenants a month I need to drop a message to. I know my old PM would never do this probably because the property manager got to keep the late fees so they didnt mind them paying late. I like to keep good communication with my tenants but is this necessary?

Should I be more robotic and let the management software do its work?