Part of the problem with repeated plays of the same song on the touch is the poor quality of the shuffle. What I've experienced is that it's not a truly arbitrary shuffle; it keeps shuffling the same tunes over a fairly limited song cycle. But recently I've discovered that rather than selecting "Songs" one selects "Genres," and then selects a particular genre such as "Alternative & Punk," as I did last week; then using the shuffle function at this point one gets a much more "true" shuffle. I've listened to songs the last few days that I haven't heard since I programmed the touch last summer.
Two songs from No Thanks! The '70s Punk Rebellion have surprised me, and I don't know why because I've heard them many times before. On Monday I listened to The Mekons "Where Were You?" as if for the first time. Then today it was "I Love Livin' In The City" by Fear. When I was an undergraduate Lee Ving was a big deal. I had a number of friends from Los Angeles and each seemed to have a copy of The Record. And of course everyone regardless of his or her city of origin had seen The Decline of Western Civilization at least twice.