Late rent - habitual

[Sam Leon]

I have never had someone who pays late all the time.

In the past I had a few tenant late a few days here and there, and even though I have it in the lease a late fee after the 3rd day, I have never enforced it.

But this tenant is late a lot, first year he was on time on month #1, then after that late a few days to late 15 days once. "Oh I mailed it, you didn't get it? I'll mail it again if you want." and he didn't want to set up direct deposit either.

At first I thought it's the lease due date which was 27th of each month because he moved in that day and threw things off. Lease renewal for year #2 I pro-rated his rent and started it on the 1st.

Same problem.

Had two conversations with him. "no problem, I'll mail it earlier". No change.

I started to mail him a letter with a late fee, then I got a check without the late fee. He claimed the notice didn't get there when he mailed the check and didn't pay. So now we have three months where he didn't pay late fee, on month #4 now and today is the 8th and no rent check yet.

I am sick of it and don't want to be the one sending email reminders and text.

Should I start to evict him for paying late?

Any sample letter I can use?