Turnovers and Late Paying Tenants

[Carlos Rovira]

I am being presented with quite the dilemma and I'd like to poll the BP community to decide what I'm going to do:

I currently have a tenant in one of my smaller units that consistently pays late. There has not been one time that this tenant has paid on time. He always ends up paying and pays the late fees but usually pays late, sometimes close to 10 days late, after I call and send emails, texts, etc. It is an inconvenience for me from a property management perspective having to go through this "collection" ritual every month, yet at the same time manageable, since he does end up paying. The guy seems to have a strange "pay" schedule from work so he doesn't always have enough cash to pay exactly on time and then does pay once he gets paid.

The dilemma is as follows: His lease is up in 60 days. Do I kick him out and deal with the cost of a vacancy/turnover or do I keep him as a month to month and continue to deal with his late payments? There is also the risk that a new tenant will be the same although having costed me more in turnover.

Looking forward to hearing some thoughts.