Though this is another entry perhaps more appropriate for Playlistmag.com, I’ve seen enough hand-wringing over this one in Macworld’s forums that it’s also worth examining here. The issue is what one should do when an iTunes music library has been vaporized due to a hard drive crash and a copy of that library exists on an iPod.
Apple’s legal department would prefer that, faced with such a situation, you re-rip your CDs to iTunes and re-purchase any music you bought from the iTunes Music Store. While I understand why Apple’s legal beagles favor these options (Apple has taken some care to make moving music between a computer and the iPod a one-way operation), most sane people recognize that re-ripping and repurchasing music is both inconvenient and expensive, particularly when a backup of that music exists on the iPod.
So what to do? There are any number of utilities that can copy music from an iPod to your Mac. Of those, I’m keen on The Little Appfactory’s $10 iPodRip. I also like CrispSofties’ iPod.iTunes, but given its 29.90 euros price and the current wretched state of the dollar (thanks to which the utility costs nearly $40), it’s a little tough to justify the expense.
I prefer these utilities because they not only copy all the music from your iPod to your Mac — including music purchased from the iTunes Music Store and audiobooks — but do so while maintaining the playlists you’ve so carefully wrought.