Open Source Alternatives to iTunes: Your Favorite?
While it's true that Apple iTunes has some compelling services, such as their TV/music/movie store, the media player itself leaves many power users yearning for something more.
To be sure, the alternatives don’t have Apple's muscle with the media industry. This translates into a lack of a movie/TV download service to be seriously competitive with the likes of what iTunes can provide. Despite this drawback, there are still some great open source alternatives to iTunes for those who are more interested in software freedom than software convenience.
Songbird – Without question, this is one of my favorite open source alternatives to iTunes. Despite still being under heavy development, today's Songbird application is cross platform and easy to use. And for those who have an iPod or MTP device such as a Creative Zen, it’s a smart match from the start.
On the flip side, however, newer iPod Nanos and the iPod Touch are not currently working with Songbird. Hopefully this will change in the future, but I tend to think it’ll be a ways off.

iTunes Alternatives
I bought an iPod Touch last July and I really love this gadget. Unfortunately, it is the only reason I still have a dual booting machine. The firmware can only be updated with iTunes. iTunes will install with WINE but will not SYNC. This is not good. Updates from Apple are not infrequent and all have been worthwhile.
Some people have "jailbroken" their devices. This will allow Amarok and others to work, but again you will have problems with updates.
For now, I can't get rid of iTunes but here are two methods of getting music out of your gadget without iTunes.
First, there are some apps that let you use your device for remote storage, kind of like a thumb drive. You move your music files to a folder on the device with a WiFi connection. They will play individually. No playlists, no album art, no features, just music. The app I use is called AirSharing. It costs less than $10. There is another called Discover that works as well and is free.
Second, are a number of Internet Radio Station players. Of course you will need wireless access to use these. Some players like Pandora and Slacker allow you to customize the music to your own tastes. Other players include AOL, FlyCast and Stitcher. All are free.
The iPhone/iPod Touch are very popular devices. The are many third party developers (hackers) working on the problem. Unlike the blogger, I tend to think that a solution is near at hand and that solution will hopefully work in Linux.
iTunes
While I am sympathetic to your problems it highlights the first rule of Linux use, that is check for compatibility before you buy. I have several Creative Zens across the family and I personally have an iRiver. They all function properly under Linux, my iRiver has been modified with Rockbox software. iPods are made by Apple to make money for Apple and they go out of their way to make it hard to use anything but their software, and I am not a fan of their software anyway. If you buy DRM encumbered songs from iTunes then you are stuck forever with the Apple hardware/software combination, or trash songs you have paid for - a great business plan but not a great plan for individual consumers. The chances of a Linux native iTunes is zero.
Whether it is a music player or a wifi card or any other bit of hardware, a few minutes with Google can save Linux users a lot of grief.
http://anythingbutipod.com/ has a large amount of info for your next music player. There are now many MP3 stores offering DRM free music, I have no experience with iTunes DRM free music but I would guess you still have to use iTunes to enter the store. I am sure you are correct in that they will eventually crack the code and make the Touch useable with Amarok etc, but by then Apple will have bought out a newer player and the game starts again. The only solution is to jump off the treadmill and avoid iPods.
GregE
Melbourne, Australia