Thank you all for your quick responses. Very helpful.
@Jacob Coates I did go and speak with her face-to-face in January. At that time, I was very clear about expectations and we managed to work out a solution where I received January rents (late of course). That said, she hasn't been nearly as responsive to my communications in February. She says she can't hear me on the phone because it's broken (ironically, though, she can hear all of my voice messages). I also want to be careful not to cross the boundary of what a judge might consider as harassment.
@Gerald K. we have a 15 month lease (wanted the lease to terminate in the Spring) so we still have another year ahead of us. We would need a reason to terminate, and even then, I'm afraid the judge might grant her the right to stay in the property until the end of the school year when she gives him her sob story.
@Jason McGuire cGuire I agree that $9.11 isn't worth filing for eviction over. I just thought it might give me a head start on eviction since this woman likely won't be able to pay March rent, and she is virtually judgement proof so I won't be able to collect back-due rent if I let it accrue. Like Patrick said, I am worried that tenant-friendly judge would shoot me down in court for starting eviction over $9.11 even if she is late on March rent and has never paid on time.
@Patrick L. I've thought about your suggestion of a mutual termination of the lease. This may be especially attractive to her given that the security deposit didn't come from her (it came from the shelter that placed her). Also, she has already indicated via text that she plans to move out in June after the school year finishes because I'm such a "negative" individual (threatening eviction and all). Any suggestions on how to make such an offer if she won't take my calls? I don't really want to put this in writing for fear of how a judge may perceive it, given that she almost paid due on February rent.
@Troy Fisher Excellent idea. I was worried about the precedent. I will definitely be doing this. Any suggestions if she refuses to sign for a certified letter?
@Andrea M. Thanks for the advice. Very helpful to be coming from somebody in VA, too. If you can evict after two late payments in VA, does that mean I can accept a second late payment and then evict, or do I have to forgo eviction if I accept payment? Any experiences with evicting based on partial payment of rent? Did the judge have any problems with that?
@Wade Sikkink I couldn't agree more about being firm. Like you said, I think she is just testing the limits to see what I will do by leaving $9.11 unpaid. Did you need to get a "Release of Rights to Possession" form signed when your tenant vacated? Is that even necessary after posting a "Pay or Vacate Notice"?
@Aly L That is a good idea to bring someone along. I'll do that if I can arrange a meeting.
Thank you all for the help, I'm very grateful. Has anybody here had nightmare scenarios in which a judge did find in favor of an unruly, judgement-proof tenant with back-due rent?