If all goes as planned, my roommate will be completely moved out by the end of the day on Sunday. I have to admit, even with the loss of income, I'm relieved. She's a good friend, but she's definitely a bad roommate.
I did learn some things from this experience, however.
Because she was an old friend, we didn't make any sort of formal agreements as to her lease or her responsibilities. She wasn't ever added to my lease (which I don't regret) but we had no written agreement and our only real verbal agreement was "You will pay me $X rent on the first of every month."
I should have better spelled out the household responsibilities. I thought that was a given, but we clearly needed to have a chore list. I know that's common in group houses, just because there are so many people living there that it's just easier to dole out the chores rather than wait and see who does what. I just didn't think it would be an issue in a two bedroom apartment.
I should have had her provide a security deposit. Not that she did a significant amount of damage to things, but I have asked her to make sure she cleans everything before she moves out. I am not convinced that this will happen. Most notably, she has been using my bedding for the past year. While I am okay with that (it was bedding I used on the spare bed anyway), I requested that she take the comforter to the dry cleaner's before she leaves. As of yet, the comforter is still in the apartment. If she doesn't take it or offer money, I will be asking her for the money for the dry cleaning, but I hate to have to do that. As for the other cleaning, if she doesn't do it, I'm pretty much stuck. The threat of not returning her security deposit likely would have helped inspire her to clean. And if it didn't, well, at least I'd have some extra cash to ease the frustration of cleaning up after her.
On the other hand, from my point of view, it's good she didn't have a year long lease with me. She wouldn't have signed it, since she wanted to move, but I also wouldn't have been able to finally ask her to move when things got bad. So that was possibly a mistake on her part. I do think that my words were just the motivation she needed to actually start looking - she's wanted to move to a "nicer" (read: more expensive) neighborhood for a while now.
So, lesson learned. I'm not sure what my next steps are. I won't be getting a new roommate before the holidays, but next year, I'll probably start looking to see who's out there. And hope that the next one will be better.