Considerations when raising rent after 1 year of renting

[Dan V.]

I am considering raising rent. 3 important details I am considering:

1) Currently, rent is below market value

Property is located in a desirable area in South Florida. I gave her lower rent than any other properties in the zip code. Currently, I charge $1350, but I looked on realtor.com and zillow.com today, and for a comparable house with a private driveway and fenced back yard, where the house is only 100 square feet larger with the same number of rooms and bathroom, they are asking $1750 per month. The cheapest thing I could find in this zip code was a condo with no yard and house was same same size and same number of rooms and even for this condo they are asking $1575.

2) Tenant complained often in beginning, but not in previous 4 months and keeps house clean

First 4 months tenant complained often, but past 4 months she has not complained. This is South Florida, and hence we were hit by Hurricane Irma in 2017. The fence went down and she has large dog and said she needed a new fence immediately. Also, she complained first 4 months about toilet being clogged on 3 separate occasions. After I got frustrated, she stopped calling me so much. She does keep house clean.

3) Tenant often struggled to pay current rent, sometimes 10 days late for rent but not beyond that

This is probably my biggest concern about the tenant. She has her 12-year old child living there (which is fine) but also her “boyfriend”. She says her boyfriend isn’t working. She is bringing all the income for the entire household and few months ago she was in hospital. And was paying rent late. Can she afford a rent increase? I have my doubts.

All these factors make for a tough situation. How much should I raise rent by or should I tell her to move out and find a new tenant?