You're just adding an unhealthy dollop of chronic stress to her life.

I'd be inclined to non-renew a tenant who is chronically late and has returned checks however, regardless of the math.

If it is chronic, tell them it isn't working out and suggest they find another place to live.  

What do you do with chronic late tenants?

Ignore their cries about you neglecting them and their requests for discounts, or at most, reply "no".A couple times I've had chronic complainers in units I knew I could rerent very fast, and I've told them something like this: "Listen, it sounds like you aren't happy with the home.

While I am unfamiliar with the markets in the other neighborhoods you mentioned, I have looked into West Hill and it was something I decided against as I personally did not get the feeling of "hey, I want to live here" due to what seems to be chronic property neglect by other owners in the area.

Still get chronic complainers and threats.

The local market, he said, is outpacing the mid-2000s housing boom.With the exception of a few urban markets, including Manhattan and San Francisco, the U.S. is seeing “a chronic shortage of inventory, heavy sales volume and prices rising at levels wildly ahead of income growth,” said Jonathan Miller of New York-based Miller Samuel Real Estate Appraisers and Consultants.

Perfect for BRRRR.Now Milwaukee is dealing with a chronic housing shortage, extremely low inventory and with that even very dated houses will not get a meaningful discount.

The only material recourse in a situation where a tenant is chronically late but ignores late fees is to non-renew their lease when it expires and take the late fees out of the security deposit (but this also can get sticky if there is damage to the property, and the cost of repairs exceeds the deposit.)