First ever perpetually late paying tenant - help/ideas

[Kuriakos Mellos]

Hi BP community!

After hitting a very solid stretch of on time payments across my portfolio over the last 3 years, I’ve run into an issue with one of my LTRs where I have a tenant who now pays late every month.  I’m not saying a day or two or five - but usually the third or last week of the month.  She does pay the late fee when she pays.  It’s a one year lease, we are in month 4 - still yet to pay for February - but more so worried that this will start dragging into a month late or more.  
Again up to this point been lucky with great tenants across my 8 units - so maybe I’m over thinking here, and she is pleasant in person and keeps her area generally cleanish.  

However the excuses she has (and I’m sure we could all write a book about them) are, how to say it kindly, laughable almost.

I usually get a text saying she will pay by a certain date, which passes and left her a voicemail today asking to talk - I am trying to be understanding and said let’s talk on the phone to discuss a plan, but at the same time - don’t want to keep someone around that is not going to follow their lease terms.

Questions:

How often is it OK to ping a tenant for late rent?  Every few days?

If I see this continuing do I offer a a cash for keys situation to just get her out?  

Maybe I’m overthinking but trying to get ahead of any issues - thanks!

[Nathan Gesner]

Quote from @Kuriakos Mellos:

My advice is very simple: get her out as quickly as possible.

She can't afford the rent. It doesn't matter why. If you think $50 in late fees is enough to offset your risk, you are in for a rude awakening.

By accepting these late payments, you are giving her the impression your rules are negotiable or unimportant. You are also lulling yourself into the false idea that she will "always pay eventually." There will come a day when she's a month late and you'll lie to yourself that "she always catches up" and "at least I'll earn an extra $50 in late fees" but then the money never comes. And when you finally decide to get serious, she will disappear because the reason she stopped paying you is so she could save up money for the next sucker. Your "generally cleanish" tenant will leave you a mess to clean up, you'll lose a couple months of rent and utilities, and you'll realize that a $50 late fee isn't extra income.

Don't reward her with cash for keys. Wisconsin does not have a grace period, which means you can start the eviction process on the second day of the month (or whatever your lease allows). I would start the eviction on the very first day you are allowed, and stick with it to the end. Either she pays on time or she moves out, period.