Inherited tenant, behind on rent, no deposit or last months rent

[Christian S.]

My tenant has a history of being behind and I have not been able to remove him from the property yet. I should raise rents from $1000 to $1400 but I want back rent first. Last winter to catch up on rent he did a bathroom remodel for me at a great rate. He is currently behind by $1200 again, with 1k more due next week. I haven't lived in the area lately and admittedly have been doing a poor job at managing from a distance.

I now know to issue a pay or vacate immediately on late payment, -but how do I get a tenant to pay me back when he is already behind?

It is tricky because I feel like he has an edge on me without any kind of deposit/last month rent.

I am considering some kind of agreement with him working in his unit for a set time, at the end of which rent goes up. The advantage being the unit is rented while the work gets done, he catches up on back rent, and he possibly earns money for finding a new place.

I don't have a means of issuing letters while I'm away from town so we've been texting. How should I document the late rent?

Go easy ya'all, I know I'm making lots of mistakes here, I went from renter to managing three units and I just haven't been able to handle this one wildcard.