I went out for a 20 mile run today (yay me) wearing my handy dandy Sansa 4MG Clip, a little Mp3 player that is cheap and generally quite good. Last night, in preparation, I set up a playlist that was 3 hours long because I was hoping to be running for 3 hours. I loaded it with heaps of Old Fashioned Goodness and New Fangled Coolness and was looking forward to listening as I ran. I got out, started running, and about 10 miles in (or an hour and a half) something annoying happened - my playlist restarted at the beginning. Sadly, I knew what that meant. Only half of the playlist had made it onto my MP3 player last night when I synched it. WTF? This same thing happened to me 2 weeks ago in my last 20 mile run, only then it was 1 hour into the run (so I heard the same set of songs 3 times before I was done).
Now this is probably because I'm using Songbird for my media player, which I generally like because it's freeware, it's not Microsoft, and it has a lot of functionality to it. But it is very newly developed and so glitches clearly remain (like not downloading songs right to my MP3 player). I would use Windows Media Player except that for some reason any time I hook my Sansa up to the USB port Media Player freezes. I've tried updating Media Player, updating the firmware on the Sansa, and numerous web searches. To no avail. So I went to Songbird and get this crap. It's not that I don't like the first hour (or hour and a half) of the playlists I put together - I like them a lot, or I wouldn't put the songs on. It's just that I like the songs that didn't make it onto the Clip just as much. In fact for today I had the songs set up in an order where the slower, so so songs were at the start and then the coolest songs, like TV on the Radio, were at the end (when you really really need good songs). So, well, poop.
I'll go find some other freeware players that can synch with MP3 players. I truly have no doubt that eventually the Songbird development team will get this right, but I want my MP3 (get it? Like MTV?? get it??). I'll let you guys know when I find a good alternative.