So, I admit this, the wife has a iPod. She wanted it to integrate with the Sync system in the truck... After many painstaking hours of putting all the music she wanted on there originally and then weeding out the stuff she decided she didn't want after all (this is all MP3s that I ripped from my own CD collection and hers) very few that were bought off iTunes. Now, she tells me she wants more songs on there from new CDs that we bought. I plug it in and am prompted to update the firmware on the iPod. It will completely wipe all songs off the iPod and I will have to spend all those hours putting the songs back on there because Apple decided that they want to encode everything on the iPod. Yes, I know I can jailbreak it, but I don't feel like learning how to jailbreak because this is the only piece of Apple technology I will ever own. I also know that there is software that will pull the songs off of the iPod but the free ones lose the embedded info and the pay ones are not free.
Long story short. My wife's iPod is just another fragmented device on an old software version because Apple wants me to buy everything off iTunes. I will never update the firmware.
That is part of their problem. They force you to delete everything on the device, not just update the software. They were a match made in heaven with the evil empire of AT&T.