Tenant Problem / Novice Landlord

I have 2 Fairly descent Tenants in my 3 family Brownstone. Impecably kept. Problem is they seem to think it is my responsibility to track them down to get the rent as opposed to them Making sure it is to me on the 1st of each month.

What can I do? The lease agreement has language that states a $50 late fee will be assessed if the rent is received after the 5th of the month. I have yet to enforce that.

On top of this, 1 tenant started with just herself and her young son. NOW, it’s her, her young son, and her “gentlman caller” Who now even shares the same checking account?

I have no idea what I should do or can do.
Any advice is Welcomed!!!!

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