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We used Senuti (iTunes spelled backwards) which allows you to transfer songs from your iPod to your computer. It worked fairly well. I had used Senuti once before to move music from my daughter's iPod to her MacBook (running Tiger).
Tansferring songs on a Tiger machine was simple. We could select all the songs at once and click on transfer. But Leopard offered us a challenge. We could only transfer about 50 songs at once. When we tried more than that, the transfer did not work. I do not know if this is a Leopard bug or a Senuti bug. Nevertheless, the songs are transferred and Aaron is happy with the result.
Senuti has written explicit instructions on how to transfer music from your iPod to your computer, so be sure to read them before you use it.