On her 1997 double live album, Living In Clip, Ani DiFranco introduces this song as "a little snippet of the folksinger at 18", eliciting squeals of delight from her appreciative audience (most of whom were probably thinking, as I do every time I listen to this track, "Mmmm, folksinger at 18"). Between the 5th and 6th verses, she pauses to comment, "So, this one was really big in the little folk clubs in the West Village. They loved me there, yes indeedy.... I'd go to the open mic nights and alienate everybody."
When I saw Ani perform this song in May 2000, she referred to it as "a security blanket of a song", explaining that every so often she writes herself something that can be performed as a defense against hostile audiences. "Out of Habit"'s punch line, "Fuck this time and place", which she repeated to us with a big conspiratorial grin, certainly succeeds as such a weapon.
Finally, I've read an interview with DiFranco in which she said that she wrote the line "My cunt is built like a wound that won't heal" as a deliberate attempt to reclaim the word cunt into loving and affectionate use (big bonus points to anyone who's read this and can tell me enough information that I can track down her words and cite them appropriately!) Whether she succeeds is open to interpretation, but either way I'm sure Inga Muscio would be proud.