I haven't played with 2.0 yet, but I could do this with a 60 gig wheel Ipod, by just putting it in a speaker dock and setting the alarm to silent, then pressing play and then turning it off.
when the alarm triggers it turns back on and resumes playing.
I used this to wake up a dorm of Stag's ( uk term sorry) with the joys of the "eagle has landed film" before a day's shooting.
steve