A Multiplicity of Devices

Yes... I know I'm a geek. I get this. I know I have a "few" devices around the house. But why does it have to be so difficult to get the same music on multiple places?

I have an older Creative Zen Jukebox with a 60GB drive in it. It has more than enough room to hold my entire library but it doesn't support any format except WAV, MP3 and WMA. It does have some features that I love for listening to music like the ability to have a free-form "now playing" list that you can add to. So you could say browse for an Album, add it to "Now Playing" find another album, add IT to "Now Playing" and so on. Thus creating a free form playlist of say 5 albums you want to listen to now. It also has an "All Play" mode that basically goes through everything on the jukebox which I LOVE for it's "oh yeah... I love this song... I almost forgot I had it..."

On the other hand, I have a first generation 2GB iPod Nano which I love for it's portability (it's much smaller than the Zen). It supports WAV, MP3, AAC and Apple Lossless. This one I love almost more for it's integration with iTunes pod fetching. I use it almost exclusively for listening to Podcasts. Although I do have some Audible Books that I have on there as well.

We do own a fourth generation iPod Photo but I don't use it because I don't like the way you navigate the music and for video... well none of the video we have plays on it. Not to mention the fact that it is noticeably slower than the Nano OR the Zen. Which means I can't just blame it on the hard drive as the Zen is also hard drive based.

So what's my dilemma? Well I want to be able to have the reasonably highest quality music I can, with album art, and tags on as many devices as I can without a lot of work. I would go to Apple Lossless if I didn't have the Zen. I could just stay in MP3 format but iTunes is less than perfect in it's support of tag writing (it doesn't seem to want to write the tags to the files, instead preferring to keep everything in it's own metadata / library file). I would dump iTunes and it's idiotic dependence on play lists to manage groups of music except that I can't find anything better that also does pod catching. Anything else good at pod catching doesn't seem to have good support for both the Zen and the iPods. The only format all the devices support is MP3 but as mentioned iTunes is a little schizophrenic about MP3 but I can't replace iTunes...