I sent him a three-day notice and raised his late fee to $100 because he has been chronically late every month.

The chronic late payers were not happy that we were enforcing timely payment and late fees.  

Not destructive, dangerous, etc but chronically late and always someone else's fault.  

My experience: often this "offer" is made when a tenant is having difficulty coming up with rent, either short term or on a chronic basis.

Adam, you cannot be lenient, it does not matter if you have 21 or 2100 units, you have to have firm rules and a system that is consistent, send a strong message and is willing to move forward with the next steps if need be, in the same respect if the tenants have been in the units for a long time and now have started slipping you have to ask yourself, if something happened to them and if this is an isolated incident or has this become or always has been a chronic issue.

I've had to evict one group of renters, and they caused some damage, which they paid for, but another set of renters are chronically late.

In the other extreme, the area may have chronically high ground water and or low percolating soils and you're fighting it each year.

If she is very sick with a chronic illness a social worker may already be involved. 

Not to get too deep into health issues but I do believe chronic stress and pressure weighed in on my personal situation.

I have a tenant that is chronically late on her rent payments.