Should I Offer to Extend Rent Due Date?

[Cassie Chun]

I’ve noticed that one of my tenants consistently pays the rent on the 5th of each month. My lease states that rent is due on the 1st of the month with a 3 day grace period (this tenant specifically asked for 3 days). I’m guessing pay day is on the 5th. On the 5th of each month I get rent + late fee automatically deposited into my account. Should I offer to extend the grace period to coincide with pay day? I feel bad about collecting a late fee each month for rent being 1 day late, especially for someone who appears to be living paycheck to paycheck.

If anyone has experience with this specific situation and decided to be more accommodating, how did things work out?