Confessions of a reluctant runner. Part 2, Musically inclined

So, I've been running for a while now, and for some reason I've never included music to my outings.  Alright, the reason is I've been too cheap to pick up an iPod for myself.  Anyway, up to this point the only thing I've been listening to is the sound of my own breathing.  For the most part I was fine with this arrangement.  Listening to my breathing had forced me to concentrate on my pacing and my effort.
A couple of weeks ago I started taking an old iPod on my runs.  I couldn't believe the difference!  The music made me feel more energized, made the run feel less tedious, and made the whole experience just better.  I was worried about the distraction that it would cause, but it turns out the distraction was a pleasant one.  I was surprised how much the music affected me.  There's only been one small glitch.  The iPod I use freezes in the cold temperature.  So while I'm enjoying the music, it only lasts part way through my run.  Even so, I seem to be able to continue on the same pace, using the memory of the music to push me along.
As a result, I now want to have music on all my runs.  In fact, I'm quite excited to see what may happen with my longer distances.  It would be interesting to see if the addition of music will help me through the inevitable mental and physical roadblocks that pop up during a long distance run.  I'll also have to spend some time constructing the perfect playlists for my runs.  However, before that can happen, I need to find an iPod, and possible accessory, that will allow me to run in the cold without it freezing up on me.  Obviously, Apple needs to invest a little more in Canadian content when it comes to R&D.
Now, to construct the perfect running playlist...