When to know it’s time to remove a tenant

[Eric Skiba]

Hi all, 

First time posting here! Some good information on this site. 

I have a question I would like to get everyone’s opinion on. I have a tenant who will be going on 2 years living at my rental. For the first year he was always paying on the first of the month. Now, he’s been 2-3 days late and currently still hasn’t paid for this month. This is after numerous emails, and texts to him that have gone unanswered. I know he reads the emails and texts because he has answered them in the past. 

My question is, how do you guys judge when it’s time to tell the tenant to hit the road? I feel like this is one of those “what you feel is right, is right” moments, and I have been increasingly feeling like it’s time to say see ya, but the data doesn’t besides this one month. 

Side note, the guy is an emotional roller coaster sometimes. It seems like he try’s to “show me a lesson” by not paying the rent on time if he finds out I was on vacation, or finds out I bought a new home. He has made comments in the past that paint that picture so it’s not a full assumption. Thanks for the input!