I have to admit that I bought my 5GB iPod partly because on ipodlounge.com people sounded like they were having so much fun with them. i really wasn't sure what I'd really do with it. After having it awhile, it has reawakened my interest in my music.
1. I can take 840 songs, currently ALL of my favorites, with me on any trip all loaded in a unit the size and volume of a pack of playing cards (about a third the size of a PCDP). Try taking a comparable number of CD's on a trip. Twice the flight attendants have wanted to take it with them after seeing it!
2. With a cassette adapter I play them in the rental cars I've used since I got the unit, including a 4 day roundtrip drive from Denver to Santa Cruz to take my daughter to college. In fact on that 4 day trip I finally heard a repeat song within an hour of coming back home. There are 56.5 hours of songs on the unit! The unit can be dealt with with one hand even while driving.
3. Sound quality is fine on the road, well, as good as the system in the car, and in flight I use a pair of Noisebusters (cheap noise canceling cans) and they work well for me.
4. At home selecting a set of tunes is exceptionally easy since I don't have to plow through hundreds of CG's to get what I want and using playlists I can build combinations of songs to listen to that are ready at the push of a button.
5. After being delighted with the clear sound from the Apple buds I got interested in the reviews from this site and got a pair of Grado SR80's and now really enjoy the headphone experience.
6. I don't notice the lack of a lineout, I use the headphone jack into my CD or AUX line inputs on my receiver and while the iPod sound seems a touch shallower when A-B'ing between the CD player and the iPod I suspect that using a higher setting in iTunes when I rip my CD's might take care of the difference. But the difference just isn't worth it.
7. Finally, the Firewire interface makes downloading very quick and painless. Copying 4.5 GB from my Mac to the iPod was just minutes! In fact I now have a set of the tunes on a Mac at work, on laptop, and on a desktop at home that all play nicely with iTunes and speakers.
So if you've read this far I hope this helped, but for me, the point of the iPod is to make great music as easily accesssible as possible and it succeeds admirably! Music has never been so portable and so convenient with so little tradeoff in fidelity.