I have the 20 gig iPod. I have iTrip and the Belkin FM tunecaster. I haven't been very successful with the iTrip. I have difficulty in programming a station for it to broadcast over. I have more success with the tunecaster. The only problem is the tunecaster only gives you 4 stations to select from. If those stations have a strong signal then you are out of luck. With the iTrip you can select from a number of stations. I'm still working on mastering it.
The headphones that come with the iPod aren't the best. I use some I already had with another walkman I had.
I am extremely satisfied with my iPod. I use it when I workout and studying in a public place. I have several playlists setup so I don't have to keep selecting various artists.
I sync it with m iBook and my entire address book is on it as well.