iTunes has a way of being both really well-designed and really poorly-designed. While it manages all your music really well, it's very easy to screw up the software's sync with the actual source location of your music files, resulting in some pretty frustrating headaches. My most recent probably with the software dates all the way back to August, when my computer's disc drive was having difficulties and I had to take it into the shop for repairs. Now, although I knew better, I tried to reconnect my iTunes library (which is on an external hard drive) to my other computer, an old PC.
Bad move. In addition to having to reformat the whole collection to make it compatible with my PC, the sync file got a bit confused as to what was actually supposed to be in my collection, so by the time I had gotten my Mac back, my iTunes library was toast. Well, although I wouldn't have to re-upload my entire collection to fix the problem, I knew it was still going to be a headache, so I put it off until now, when I have to have my iPod for my lengthy flights to and from Vancouver.
As it turns out, although it was fairly time-consuming, the whole process was easier than I thought it would be, and now I've even updated my iPod so it's more or less in sync with my computer. That said, I haven't touched over half of my music collection (the stuff I'm less likely to actually listen to on the trip), so I've got a lot of work in front of me. Right now though, I'm content and ready for my flight!
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