I received my iPod on Wednesday and wanted to briefly share my first impressions (mind you, I have only used it for about 2 days now, and I haven't really had a chance to load it up yet).
The iPod is a very nice gadget. It is extremely well made and has a very intuitive user interface. My 60GB version should have enough space to store my entire mp3 collection, as well as the remaining CDs that I haven't had a chance to rip to mp3 yet. The main challenge with this huge amount of data is how easy it is to access it from the iPod.
Both the iPod and iTunes rely heavily on ID3 tags. In theory, this is very nice, as it means that we're not constrained by file names and folder hierarchies. On the down side, this works only when all mp3s have proper ID3 tags and causes annoying side effects when this isn't the case (which is unfortunately the case for many of my mp3s). For example, my mp3 file names are normally prefixed with the track number, ensuring that they always get displayed in the proper order in the filesystem, as well as by most mp3 applications (e.g. Winamp). The iPod seems to rely purely on the track number in the ID3 tag. When this doesn't exist, it resorts to sorting the tracks alphabetically by title, rather than by file name (in fact, once a song is uploaded to the iPod, it no longer has a notion of file name), resulting in a random (for all intents and purposes) order that bears no resemblence to the proper order.
This is probably my biggest gripe so far, although there are some related problems. Songs from the same album are only properly grouped together when all songs have the correct ID3 album tag. If even one of the album names contains a typo, the iPod considers it a different album and both show up in the album list, each containing only those songs with matching album ID3 tags.
Ultimately, I believe that this approach will end up working well for me. In the mean time, I guess I have to bite the bullet and clean up my mp3 collection. Luckily, there are several promising ID3 tag management applications (both for Windows and Linux) as well as services (such as freedb and MusicBrainz) that provide metadata for music and even (in case of MusicBrainz, although I haven't tried it yet) claim to be able to automatically identify a song based on a signature that is calculated from the mp3.
On the positive side: As I went with the 60GB version, I am planning on simply syncing my entire music collection to the iPod (rather than picking individual albums and songs), which should make it really easy to simply re-sync everything whenever I've made significant updates to the ID3 tags. Until then, I guess I can live with a little bit of chaos in my music collection.