I liked the idea of using iCal, but it was easy enough to use automator to get the same results without having to worry about how many tracks are in the playlist and changing the script every time I add tracks.

One thing does still bother me about using iCal this way. I can make one repeating event that only applies to certain days of the week and it's not a problem that my computer wakes up when there really isn't an alarm to play as it will simply go back to sleep in a few minutes, but what are you supposed to do if you have a later or earlier wake-up time a couple days a week? It would be nice if iCal could wake my portable as long as the screen was up. I suppose I could use the desktop to send music through Airtunes to the speakers in my room, setting it to never go to sleep, but that's going to be torture if I need to walk into an entirely different room to turn the music off. Yes, I can use the remote to turn off the speakers, but that eventually will lead to me leaving music running with the speakers muted. All I need is for a cordless phone/microwave incident to switch things back to computer speakers and I've got a nasty phone call from home right in the middle of work.

If it's possible to communicate with iCal through Applescript, it should be possible to write a program that will check to see what the next iCal alarm is and wake the computer so that whatever the alert is occurs at the appropriate time instead of the next time you manually wake the computer.

If not this, it sure would be nice if you could at least have different wake times for different days.