Dylan wrote this song in the form of a letter to a landlord, explaining that he's working hard to meet his obligations and requesting some leniency. This being Dylan, there's a lot of empathy in the letter, as he understands that the landlord is suffering as well.
You didn't think this was about a rent dispute, did you? Seems there's much more to it.
In his book Small Town Talk, Barney Hoskyns contends that some of Bob Dylan's "Landlord" songs for the John Wesley Harding album were cathartic ones working out emotions resulting from the musician's falling out with longtime manager Albert Grossman, who Dylan had come to believe had been ripping him off both financially and personally. The most transparent of these tunes is "Dear Landlord."
In discussing the "Dear Landlord" and Grossman connection with garbogolist and Dylanologist A.J. Weberman, Dylan himself stated that the song "wasn't all the way for Al Grossman... only later, when people pointed it out to me that the song might have been written for Al Grossman, I thought, well, maybe it could've been."
Dylan later requested that A.J. Weberman not report on what he'd said about Grossman and "Dear Landlord."