I was thinking about getting an Ipod as well a few months back, but opted for a Sony minidisc player instead. Why?
1. Battery life on the Ipod is pathetic. After 8 hours, it's basically dead. So much for music on those 12-hour flights.
2. Sound quality is better (SOny's ATRAC format is supposedly better than .mp3, but the jury is still out).
3. Less fragile. Drop the Ipod and it's bye-bye hard drive. Drop the minidisc player (i have already) and chances are you'll be fine.
The drawbacks of the minidisc? Carrying discs, but theses are small and hold heaps of songs on each (i can usually fit about three cds on one disc).