A few days ago, I had an idea, which I'd forgotten about, but I really like it, so I'm going to write it down here in the hopes that I remember it when I can actually do it.
I've been watching some music lectures form Gresham College recently, and some of the works mentioned in those lectures (like Bach's Goldberg Variations or Purcell's Dido & Aeneas) are works that I have recordings of but am not too familiar with. I think I've listened to both of those works only once each (I've heard Bach's Goldberg Variations twice, but they were two different recordings, so...).
In any case, I'd like to be more familiar with those works, so I'm going to start doing something similar to how I decide which book I'm going to read next, except simplified because it doesn't take as long to listen to a piece of music as it does to read a book.
The way my books thing works is that every time I run across a reference to or a mention of a particular book that I have and haven't read yet, it gets a point, so the more talked-about books get higher on the list, and when a book hits 50 points (sometimes more because I'm already reading some from the list and raise the requirement), I start reading it. (More about that, including how I don't follow this very strictly, here.)
I'm going to start doing that for these classical pieces of music. Except it'll be more like a queue rather than a list with points. So, if I run across a mention of Schumann's Symphony No. 3, I'm going to listen to Symphony No. 3, either that day or the next day (depending on what time of day I run across the reference). If I run into references for more than one piece during a day, the second piece will wait until the next day, and so on. I'll listen to only one piece from the queue per day.
I would start this right now, but I'm still in the midst of my Collection Audit project, and - as part of that - I'm trying to get through all of my music before going back to listen to something a second time. To some degree, Collection Audit helps with my familiarity of these pieces too, but it ensures only that I listen to a particular piece at least once every two years, and I don't think that's often enough for a piece to really stick in my memory. So, once I finish with Collection Audit, I'm going to start this Classical Music Queue. Of course, when it's time to do Collection Audit again in 2016, I'll postpone the Classical Music Queue.