I use three computers. I have a desktop with all my old data, a laptop for home use and a work computer. Over the last couple of years my music library has spread across all three machines. How do I sync my iPod up with them all without losing my playlists and having to start all over?
Overwhelmed by All This Machinery
To see my guide to syncing your iPod to multiple computers,
Dear Overwhelmed by All This Machinery,
Fear not! This is a very common situation, but the answer is straightforward. I suggest you start by reading Apple's guide to using your iPod with multiple computers.
By default iPods are automatically set to sync with one iTunes library, or one computer. Luckily, you can manually manage files on your iPod across multiple devices by displaying iPod preferences in iTunes and opting to manually manage music. Then you can move files from your iTunes account to the iPod. Remember you can only authorize five computers at once to play songs purchased from the iTunes Music Store.
Syncing two computers that are not connected via network (say your home and office computers) is relatively simple because iTunes is set by default to autosync with iPods. You must, however, be sure to switch to manual mode to avoid losing files.
Senuti allows you to unlock your iPod or iTunes and copy single songs, songs grouped by artist or album, or entire playlists from an iPod into iTunes. You can purchase the application for $18 or try a free 30-day trial. You might also check out MP3tunes, which provides syncing tools and unlimited online storage space for all your music files for $40 a year.
Synchronizing iTunes manually between computers can be a laborious task. SyncOtunes can ease the chore. It's designed to sync libraries and settings, provided that the computers involved can communicate directly over a network.