For better or worse, buying an iPod also means committing to Apple's iTunes software. Apple's seamless combination of hardware, software, and online store has made it many fans, but for some folks, the iTunes way of doing things feels unbearably confining.
If you love your iPod, but can't stand being tied to iTunes, there are some compelling and capable Mac and PC iTunes alternatives that can sync with your iPod. Depending on your iPod model, you'll probably still need to keep iTunes around for firmware updates, video purchases, games, and some advanced features (calendar syncing, for instance), but there's no reason you can't sync your music and podcasts using a different program.
Each of the following media jukeboxes has its own set of advantages and disadvantages. This list isn't meant to be comprehensive (by all means, add your own suggestions in the comments section), I'm just taking an opportunity to highlight my personal favorites. Also, every application listed here is free, so there's no reason not to try them all and see what sticks.
Media Monkey http://www.mediamonkey.com/ (Download Media Monkey from Download.com)
Ideal user: File hoarders, control freaks, meticulous taggers, boutique format users (FLAC, Ogg), people with messy collections.
Pros Ideal for large, scattered collections Advanced tagging features and auto tagging Supports iPhone 3G and iPod Touch 2G Copy songs from iPod to computer Album art lookup Skinnable Podcast catcher… Read more